HK1136581B - Oligo-beta-(1,3)-glucane-(1,3)-mannose, oligo-beta-(1,3)-glucane-(1,3)-mannitol and derivatives thereof for treating diseases of the immune system, methods for preparing the same and drugs containing them - Google Patents

Abstract

The present invention relates to the use of at least one compound of the formula (I) or (II), in which Ri is H and n is an integer from 2 to 10, in the preparation of a drug for treating diseases from the group comprising tumour, cancer, viral disease, bacterial disease, fungal disease, immune system disease, auto-immune disease or disease associated with a Pimmunostimulation deficiency in human beings and warm-blood animals. The invention also relates to new products having a mannose or mannitol termination as well as a method for preparing the same.

Description

The present invention describes the use of modified oligo-β-(1,3)-glucans of formula (I) or (II) below for the preparation of useful drugs in immunostimulation-based therapies.

Glucans, which are natural products, have been extensively studied and the immunostimulating properties of some glucans are known.

The Applicant has shown, in particular in WO03/045414, that Laminarine, a polysaccharide extracted from the brown algae Laminaria digitata, has immunostimulatory activities. Laminarine is a low molecular weight polysaccharide consisting of a linear β-(1,3)-glucan main chain of 20 to 30 glucose units weakly branched at position 6, which has either a glucose (G chain) or a mannitol (M chain) entity at the terminal end.

Although the immunostimulatory activity of Laminarine has been recognised, a major disadvantage of its use for therapeutic purposes is its natural origin, as the composition of Laminarine is not constant and depends on the place of collection, the time of collection, etc.

There is therefore a real need for synthetic products with the therapeutic properties of Laminarine.

The present inventors have focused in particular on the M-group oligosaccharides present in Laminarine. In the literature it is mentioned that these oligosaccharides have a β-configuration bond between carbon 1 of the terminal glucan and a primary carbon of the mannitol residue, and can be represented as follows:

They have sought to synthesize these molecules in such a way as to make available, particularly to the pharmaceutical industry, molecules with a complete characterization and a completely elucidated structure, thus avoiding the difficulties inherent in the use of natural products as pharmaceutical products.

Unexpectedly and surprisingly, the present inventors found that the oligosaccharides of formula (I) or (II) below, which themselves have a β-link between carbon 1 of the terminal glucose and a secondary carbon of the terminal mannose or mannitol, exhibited immunostimulatory activities.

The invention therefore describes the use of at least one modified oligo-β- ((1,3) -glucan of formula (I) or (II) - What? where R1 is H or OH and n is an integer from 2 to 10, preferably from 2 to 7, and more preferably still 3, 4 or 5, for the preparation of a composition for the treatment of diseases selected from the group consisting of tumour, cancer, viral disease, bacterial disease, fungal disease, immune system disease, autoimmune disease or disease related to immunostimulation deficiency in humans and warm-blooded animals. The action of the compounds of formula (I) or (II) is related to the presence of specific receptors of these compounds on the surface of macrophages and more generally of the different populations of leukocytes. This activity is attributed to the stimulation of the body's immune-compressing cells and is measured by: The activation of NK cells, T lymphocytes, and nuclear factor κB(NF-κB; phagocytic activity; the secretion of cytokines such as interleukins (IL), TNF-α, or interferon γ; the production of reactive oxidant species such as the superoxide anion or hydrogen peroxide.

Advantageously, when in the compound of formula (II), R1 represents OH, the terminal group is a mannitol.

The mechanisms of interaction of many glucans have been widely described, but have shown often conflicting results, making it impossible to predict which glucan is the best immunomodulator.

The present invention relates to some of the derivatives of formula (I) and (II) above which are novel compounds. These new compounds are oligo-β- ((1,3) -glucan-(1,3) -mannose and oligo-β-(1,3) -glucan-(1,3) -mannitol and their deoxy derivatives in position 4, which have the general formula (I') or the general formula (II') respectively: wherein R1 represents H or OH and n is an integer from 2 to 10, preferably from 2 to 7, and more preferably still equal to 3, 4 or 5. In particular, such compounds are the following: The following shall be indicated in the column 'D' of the column 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the following entries: 'D' for the entries: 'D' for the entries: 'D' for the entries: 'D' and 'D' for the following entries: 'D' for the following entries: 'D' for the entries: 'D' and 'D' for the following entries: 'D' for the following entries: 'D' and 'D' for the following entries: 'D' and 'D' for the following entries: 'D' and 'D' for the following entries: 'D' and 'D' for the following entries 'D' and 'D' for the following entries 'D' and 'D' for the following entries 'D' entries 'D' and 'D' for the following entries 'D' and 'D' for the following entries 'D' entries 'D

These new compounds are useful as pharmaceutical compounds.

The invention therefore also concerns medicinal products containing these new compounds with at least one excipient chosen according to the chosen mode of administration and dosage.

These medicines may be medicines intended for oral, intravenous or intra-peritoneal administration.

The doses of compounds of formula (I'), (II') are dependent on the disease to be treated and the method of administration chosen.

Useful oral medications are tablets, granules, syrup, capsules, and gel.

These medicinal products may also include at least one chemotherapeutic agent selected from the group consisting of cisplatin, vinblastin, paclitaxel, taxol and its derivatives, monoclonal antibodies such as Rituximab and Cituximab.

In particular, these compounds are useful as immunomodulatory agents.

Another subject matter of the invention relates to the use of at least one compound of formula (I') or (II') for the treatment of a disease selected from the group consisting of tumor, cancer, viral disease, bacterial disease, fungal disease, immune system disease, autoimmune disease or disease related to immunostimulation deficiency, in warm-blooded animals and humans.

These compounds have an original structure since the glucanic part is connected to the mannitol residue by one of these secondary hydroxyls via a β-configuration bond. The presence of molecules of formulae (I') and (II') in which R1 represents -OH has been shown in Laminaria digita.

The chemical preparation of new compounds of formula (I') or (II') is based mainly on the epimerisation of the terminal reducing entity of the D-glucose type into a D-mannose type residue. This involves the singularisation of the reducing entity in relation to the other glucose units of the oligosaccharide and the singularisation of the hydroxyl 2 of this entity in relation to the other functions of the reducing unit. Two different synthesis routes are envisaged, an iterative synthesis and a synthesis by epimerisation of the terminal entity.

According to the first embodiment, the process of preparation of the new compounds involves a reaction between a glycosyl donor of formula (D) below and a glycosyl acceptor of formula (A) below: - What? in which m is an integer from 1 to 9, preferably 1 to 6, and preferably still equal to 2, 3 or 4; p is an integer from 0 to 9, preferably 0 to 6, and preferably still equal to 2, 3 or 4;R represents an alkyl such as ethyl, methyl, propyl or butyl, or an aryl such as phenyl or tolyl;R2 represents an allyl,Methylnaphthyl, benzyl, paramethoxybenzyl, halogen acetyl (chloroacetyl, bromoacetyl, iodoacetyl) ;R3 and R4 on the one hand and R3' and R4' on the other hand together constitute an ethyl radical, isopropyldyl, hexafluoroisopropyldyl, cyclopentyldyl, cyclohexylidyl, cycloheptyldyl, butyldyl, 1-tertiobutylethyl, benzyl, methoxybenzyl, 1-phenylbenzyl or chloroacetyl R3, R4, R3' and R4' each representing a trivalyl group independently of the other, such as trivalylbenzyl, chlorylbenzyl, benzylvulb, nitrobutylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylbenzyl, trivalylben

In this application the following abbreviations are used: The following is a list of the substances which are used in the preparation of the product:

The compound of formula (A) is advantageously - What? The compound of formula (D) is advantageously

This step of the process can be included in an iterative synthesis which differs from that described in FR2804684 by the necessary use of a first acceptor with at position 2 an orthogonal protective grouping of all other groups present on the synthesized oligomers after chain elongation, which makes regioselective epimerization possible.

This iterative synthesis can be described according to the reaction pattern (reaction pattern 1) as given below:

The reaction pattern 1 above consists of: the preparation [a'] from a compound 1 as obtained in FR2804694, of a compound 2 whose -SEt group has been replaced by a -OBn group; the substitution [a] at position 2 of -OBz by -OR5, R5 being preferably a levuloyl, and the selective deprotection [b] of the hydroxyl at position 3; the reaction between donor 1 and acceptor 4 [c], or glycosylation; possibly the selective deprotection [d] at position 3 of the hydroxyl and glycosylation between compound 1 and NaOH group 6, these two groups being repeatable until a desired number of glucose units is obtained; [OH] is the preferred levuloyl group; [OH] is the preferred periodic deprotection group; [OH] is the preferred method of de-protection; [OH] is the preferred method of de-protection; [OH] is the preferred method of de-protection; [OH] is the advantage of reducing the acetone group; [OH] is the advantage of reducing the acetone group; [OH] is the advantage of reducing the acetone group; [OH] is the advantage of reducing the acetone group; [OH] is the advantage of reducing the acetone group; [OH] is the advantage of reducing the acetone group; [OH] is the advantage of reducing the acetone; [OH] is the advantage of reducing the acetone; [OH] is the advantage of reducing the acetone; [OH] is the advantage of reducing the acetone; [OH] is the advantage of acetone; [OH] is the advantage of reducing the acetone; [OH2 is the advantage of acetone; [OH] is the advantage of acetone; [OH] is the advantage of acetone; [OH] is the advantage of acetone is the advantage of acetone; [OH] is the advantage of acetone; [OH] is the advantage of acetone is the advantage of acetone; [OH] is the advantage of acetone is the advantage of acetone is the advantage of acetone; [OH] is the advantage of acetone is the advantage of acetone; [OH] is the advantage of acetone is the advantage of acetone;

It is also possible to consider synthesis by implementing a more convergent reaction pattern, as defined below (reaction pattern 2). In this reaction scheme, the donor D is a disaccharide, or higher oligosaccharide, which is reacted with an acceptor A which is also a disaccharide or higher oligosaccharide: tri-, tetra-, penta-, as obtained as compound 6 according to reaction scheme 1.

In this second reaction scheme, preferably R' is Ac, Bz or pivaloyl and R5 is Lev.

Err1:Expecting ',' delimiter: line 1 column 122 (char 121)

A second method of production involves the preparation of new compounds by an epimeration step at position 2 of the terminal chain, which also produces deoxygenated compounds at position 4.

The reaction diagram 3 below illustrates this method of implementation: - What?

In reaction diagram 3, R7 is an ester, notably acetyl, benzoyl, pivaloyl, preferably Bz, and R8, a group orthogonal to all other protective groups, may be Bn, NAP, p-methoxybenzyl, p-methoxyphenyl, allyl, and preferably Bn, X is preferably a bromine.

This third reaction pattern consists of: the reaction [A] protects all OH groups, preferably the protective group is Bz and the reaction is then conducted with BzCl in pyridine,selective halogenation [B],preferably bromination by HBr in AcOH;elimination [C],preferably with DBU diazabicylcoundesen;addition [D],preferably with N-bromosuccinimide in MeOH;substitution in an anomalous position and elimination of the protected hydroxy group in position 4 of the terminal entity [E],preferably with Ph3PO or a Lewis acid such as silver triphlate in benzylic alcohol or any other alcohol including naphthal ethanol,protective group p-hydroxy alcohol,p-hydroxybenzylic p-hydroxybenzylic p-hydroxybenzylic p-hydroxybenzylic p-hydroxybenzylic p-hydroxybenzylic p-hydroxybenzylic p-hydroxybenzylic p-hydroxybenzylic p-hydroxybenzylic p-hydroxybenzylic p-hydroxybenzylic p-hydroxybenzylic p-hydroxybenzylic p-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy-hydroxy

The synthesis intermediates used in the processes described above are new products and the invention therefore also covers compounds of formulae (III), (IV), (V) and (VI): - What? of which: is an integer from 0 to 9, preferably 0 to 6, and preferably even more preferably 2, 3 or 4 ;R2 represents hydrogen, allyl, methylnaphthyl, benzyl, paramethoxybenzyl, halogen acetyl (chloroacetyl, bromoacetyl, iodoacetyl) ;R3 and R4 on the one hand and R'3 and R'4 on the other hand together form an ethyl radical, isopropyldyl, hexachloroisopropylfluoryl, cyclopyl, precylloxylyl, cycloheptyl butyl, butyl butyl, 1-carboxybutyl fluoryl, trivalyl butyl, trivalyl butyl, trivalyl butyl, methoxybutyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trivalyl butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival butyl, trival and trival; each of these groups may be one or more; R3 and R4, R4, R4, R4, R4, R4,

The compounds of formula (III) are the acceptor compounds A as defined above.

The invention will be further understood by the following description supplement and examples which are by no means limiting but correspond to advantageous embodiments.

Examples

Examples 1 to 7 illustrate the synthesis processes of the products of the invention, and examples 8 to 11 show the biological activity of the compounds of the invention.

EXAMPLE 1: Preparation of β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-α,β) -D-mannopyranose (product A1) according to reaction scheme 1

The products 1 and 2 are prepared according to the process described in FR 2 804 684 and Jamois, F.; Ferrières, V.; Guégan, J.-P.; Yvin, J.-C.; Plusquellec, D.; Vetvicka, V. Glycobiology 2005, 15, 393-407.

[A complex combination of hydrocarbons obtained from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of hydrocarbons from the distillation of the distillation of hydrocarbons from the distillation of the distillation of the distillation of the distillation of hydrocarbons from the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the distillation of the gas from the gas from the gas from the gas from the gas from the gas from the gas from the gas from the gas from the gas from the gas from the gas

After 5 hours of stirring at room temperature, the DCU is removed by filtration, then the medium is picked up by 50 mL of dichloromethane and washed by a 10% aqueous solution of hydrochloric acid, by an aqueous solution saturated with sodium hydrocarbonate and by an aqueous solution saturated with sodium chloride. After drying on MgSO4 from the organic phase and gel, the compound is purified on [petroleum ether/acetate; 3 v:1/v] to a concentration of 1.2 g. Product 3 : white solid; Pf (°C) 133; Rf (EP/AcOEt, 3:1) 0.4; αD20The following is a list of the substances which are to be classified as 'chemical' in the Annex to Regulation (EC) No 1907/2006 of the European Parliament and of the Council: (a) chemicals, (b) chemicals, (c) chemicals, (d) chemicals, (e) chemicals, (e) chemicals, (f) chemicals, (g) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, etc.)); chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h) chemicals, (h)

[ (b) Preparation of benzyl benzyl 4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranoside (Product 4) with a content of more than 10% by weight of benzyl benzyl acetate and a moisture content of not more than 30% by weight of benzyl acetate and/or benzyl acetate.]

In 50 mL of a dichloromethane/methanol mixture (4:1; v/v), introduce monosaccharide 3 (1,1 g, 1,844 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (810 mg, 3,568 mmol) at room temperature. After 5 hours of reaction, dilute the medium with 50 mL of dichloromethane and wash twice with a saturated aqueous solution of sodium hydrocarbonate. After purification (MgSO4) and the organic phase, the residue is purified on silica gel [research ether/ethyl acetate (3:1; v/v) ] to obtain 690 mg of the product with an efficiency of 82%. Product 4 : white solid; Pf (°C) 122; Rf (EP/AcOEt, 3:1) 0,2;αD20The following is a list of the substances which are to be classified as chemicals in the feed additive: (i) chemicals which are to be classified as chemicals in feed additives, and (ii) chemicals which are to be classified as chemicals in feed additives, and (iii) chemicals which are to be classified as chemicals in feed additives.

[ (c) Preparation of 2-O-benzoyl-4,6-O-benzylidene-3-O-(2-methylnaphthyl) -β-D-glucopyranosyl-(1→3)-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranoside from benzyl (product 5)

The medium is then added to N-iodosuccinimide (NIS) (763 mg, 3,390 mmol) and trimethylsilyl triflate (50 μL, 0,283 mmol). After 3 hours of reaction, the medium is neutralized by triethylamine, filtered into the concentrate. After purification by chromatography on silica gel [toluene/ethyl acetate (9:1; v/v) ], 2.51 g of the desired product is obtained with an efficiency of 94%. Product 5 : white solid; Pf (°C) 178-179; Rf (EP/AcOEt, 3:1) 0,2;αD20The following is a list of the substances which are to be classified as having a specific chemical composition: 21,0 (c=1,0, CH2Cl2).RMN 1H (CDCl3, 400 MHz) δ (ppm) : 7,90-7,86 (m, 2H, H arom.) ; 7,70-7,67 (m, 1H, H arom.) ; 7,60-7,21 (m, 24H, H arom.) ; 5,53 (s, 1H, H7b) ; 5,28 (s, 1H, H7a) ; 4,94 (d, 1H, H8b, JH8b-H8'b = 12,1 Hz) ; 4,84 (d, 1H, H8'b) δ (ppm) : 4,80 (d, 1H, 2H, H arom.) ; 7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-7,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,70-70,7-80,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,70,7

[ (d) Preparation of 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl- ((1→3)-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranoside from benzyl (product 6) ]

2,3-dichloro-5,6-dicyano-1,4-benzoquinone (820 mg, 3,600 mmol) is added to a solution of compound 5 (1,71 g, 1,800 mmol) in a dichloromethane/methanol mixture (4:1; v/v). After 16 hours of reaction, the medium is diluted with dichloromethane, washed with a saturated solution of sodium hydrocarbonate and water. The organic phase is dried (MgSO4), evaporated and the desired product 6 is obtained after purification on silica gel [petroleum ether/ethyl acetate (2:1; v/v) ] (1,325 g, Rdt=91%). Product 6 : white solid; Pf (°C) 214; Rf (EP/AcOEt, 2:1) 0,3;αD20The following is a list of the substances which are to be classified in the Annex to Regulation (EC) No 1907/2006 of the European Parliament and of the Council: chemicals, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food ingredients, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives, food additives

[c]- Preparation of 2-O-benzoyl-4,6-O-benzylidene-3-O- ((2-methylnaphthyl) -β-D-glucopyranosyl- ((1→3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl- ((1→3)-4,6-O-benzylidene-1-O-levulinoyl-β-D-glucopyranoside from benzyl (Product 7)

The medium is then added to N-iodosuccinimide (100 mg, 0.444 mmol) and trimethylsilyl triflate (6.7 μL, 0.037 mmol). After 2 hours of agitation, the reaction is completed and the medium is neutralized by trielamine, filtered and then concentrated. After purification by chromatography on silica gel [toluene/ethylene acetate (9:1 v/v) ], 328 trisacide 7 mg with an expected efficiency of 68% are obtained. Product 7 : white solid; Pf (°C) 115; Rf (EP/AcOEt, 2:1) 0,5;αD20The following is the list of substances which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and in Annex II to Regulation (EC) No 1907/2006:The following is the list of the substances which are to be classified in the additive: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of a mixture of: - in the form of: - in the form of a mixture of: - in the form of: - in the form of: - in the form of - in the form of - in the form of - in the form of - in the - in the form of - in the - in the - in the form of - in the - in the - in the - in the - the - in the - the - in the - in the - the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - in the - inThe number of units of measurement is calculated by the following formula:

[E]- Preparation of 2-O-benzoyl-4,6-O-benzylidene-3-O-(2-methylnaphthyl) -β-D-glucopyranosyl-(1-3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4,6-O-benzylidene-β-D-glucopyranoside from benzyl (product 12)

7.6 mL of a 1M solution of hydrazine in a pyridine/acetic acid mixture (3:2, v/v) are added drop by drop to a solution of trisaccharide 7 (500 mg, 0.383 mmol) in pyridine (7.6 mL). After 3 hours of stirring, the reaction is stopped by adding 2.1 mL of 2,4-pentane-dione and the medium is concentrated under reduced pressure. The residue is then picked up by 50 mL of dichloromethane and washed by a 10% aqueous solution of hydrochloric acid, by a saturated solution of sodium hydrocarbonate and a saturated solution of sodium chloride. After drying (SOMg4) and the product is purified by chromatography on a gel of petroleum cyanide (2:17%/v) to a concentration of 82%. Product 12 : white solid; Pf (°C) 136; Rf (EP/AcOEt, 2:1) 0,5;αD20The following is the list of substances which are to be classified as chemicals in the feed additive:The following is the list of the substances which are to be classified in the additive: 129,8, 129,7, 129,3 (C arom.) ; 129,2 (C quat. arom.) ; 129,0, 128,7, 128,5, 128,4, 128,3, 128,2, 128,0, 127,9, 127,8, 127,5, 126,7, 126,7, 126,4, 126,1, 126,0, 125,7, 125,6 (C arom.); 102,0 (C7) ; 101,2 (C7) ; 100,5 (C7) ; 73,8 (C8c) ; 71,2 (C8a) and table 3b.Elementary analysis (C71H66O18): Theoretical: C = 70,64%, H = 5,51 %; Measured: C = 70,49%, H = 5,54%.HRMS (ESI) : [M+Na] 12471H12461, 125+M/O18661, 125+M/O18661, 125+M/O1479, 125+M/O1471, 125+M/O1471, 125+M/O1471, 125+M/O1471, 125+M/O1871, 125+M/O1871, 125+M/O1861, 125+M/O1861, 125+M/O1861, 125+M/O1861, 125+M/O1861, 125+M/O1861, 125+M/O1869, C/O1869, C/O1849, C1869, C18/O1849, C1849, C18/O39; Meas measured: Theoretical: C: C/O1865, C18/O395, C18/O395, C1845, C18/O39; Meas measured: C/O1845, C1845, C18/O1865, C18; Meas measured: C18/O185, C185, C1850, C18/O39; Meas measured: C1850, C18/O185, C185, C185, C185, C185, C185, C185, C185, C185, C185, C185, C185, C185, C185, C185, C185,It's a 4040.

Preparation of 2-O-benzoyl-4,6-O-benzylidene-3-O- ((2-methylnaphthyl) -β-D-glucopyranosyl- ((1→3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl- ((1→3)-4,6-O-benzylidene-β-D-glucopyranos-2-uloside of benzyl (Product 15a) 2-O-benzoyl-4,6-O-benzylidene-3-O-(2-methylnaphthyl) -β-D-glucopyranosyl- ((1→3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl- ((1→4) -4-O-benzylidene-β-hydroxybenzyl-d-glucopyranoside of benzyl (Product 15a)

The unprotected compound 12 (330 mg, 0.273 mmol) is added with 9 mL of a DMSO/acetic acid mixture (2:1, v/v). After 48 hours of stirring at room temperature, the medium is diluted with 50 mL of dichloromethane and washed with a saturated aqueous solution of sodium hydrocarbonate and water. After concentration and several co-evaporation with toluene, the medium is purified by silica gel chromatography [petroleum ether/ethyl acetate (3:1; v/v) ] to 180 mg of the oxidised product 15a (Rdt=55%) in the mixture 2: its hydrated form with 15b. The product 15a is a white solid; Rf (EP/AcOEt, 2:1) 0.3.RMN 1H (CDCl3,The following are the main components of the test method: • the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the noise level of the vehicle, the measurement of the measurement of the vehicle, the measurement of the noise level of the vehicle, the measurement of the measurement of the vehicle, the measurement of the measurement of the vehicle, the measurement of the measurement of the vehicle, the measurement of the measurement of the vehicle, the measurement of the measurement of the vehicle, the measurement of the vehicle, the measurement of the vehicle, the measurement of the vehicle, the measurement of the vehicle, the measurement of the vehicle, the measurement of the vehicle, the measurement of the vehicle, measurement of the vehicle, measurement of the vehicle, measurThe following shall be indicated in the table of the table of the products: a) the value of the product obtained from the products of the same manufacturer, which is the same as that of the product obtained from the same manufacturer, and b) the value of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that of the product obtained from the same manufacturer, which is the same as that which was produced from the same manufacturer, which is the same as the product obtained from the same manufacturer, which is the same as the product obtained from the same manufacturer, which is the same as the product obtained from the same as the product obtained from the same manufacturer, which was the same as the product obtained from the same manufacturer, which was the same as the same as the product obtained from the product obtained from the same manufacturer, which was the same as the product obtained from the same product obtained from the same manufacturer, which was the same as the same as the product obtained from the product obtained from the same manufacturer, which was the same as the same as the product obtained from the product obtained from the same product obtained from the same manufacturer, which was the same product obtained from the same product obtained from the same product obtained from the same product obtained from the same manufacturer, which was the same product obtained from the same product obtained from the sameThe following is the list of substances which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as substances of very high concern in the Annex to Regulation (EC) No 1907/2006 and which are to Regulation (EC) No 1907/2006 and which are to be classified as substances of very low concern in the Annex to Regulation (EC) No 1907/2006 and which are to Regulation (EC) No 1907/2006 and which are to be classified as substances of very low concern in the Annex to Regulation (EC) No 1907/2006 and which are to Regulation (EC) No 1907/2006 and which are to be classified as substances of very low concern in the Annex to Regulation (EC) No 1907/2006 and which are to Regulation (EC) No 1907/2006 and which are to (EC) No 108, (EC) No 108, (EC) No 108, (EC) No 108, (EC) No 109, (EC) No 109, (EU) No 109, (EU) No 109,The following shall be reported in the table of the main components of the financial statements: (i) the total amount of the loan , including the amount of the loan , and the amount of the loan , including the amount of the loan , including the amount of the loan , including the amount of the loan , and the amount of the loan , including the amount of the loan , including the amount of the loan , including the amount of the loan , and the amount of the loan , including the amount of the loan , including the amount of the loan , and the amount of the loan , including the amount of the loan , including the amount of the loan , and the amount of the loan , including the amount of the loan , including the amount of the loan , and the amount of the loan , including the amount of the loan , and the amount of the loan , including the amount of the loan , and the amount of the loan , including the amount of the loan , and the amount of the loan , including the amount of the loan , and the amount of the loan , including the amount of the loan , and the amount of the loan , including the amount of the loan , and the amount of the loan , including the amount of the loan , and the amount of the loan , and the amount of the loan , and the amount of the loan , and the amount of the loan , and the amount of the loan , and the amount of the loan , and the amount of the loan , and the loan , and the amount of the loan , and the loan , and the amount of the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loan , and the loanThe measurement of the signal is performed at a frequency of approximately 1 Hz (see Figure 1).

[g]- Preparation of 2-O-benzoyl-4,6-O-benzylidene-3-O- ((2-methylnaphthyl) -β-D-glucopyranosyl- ((1→3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl- ((1→3)-4,6-O-benzylidene-β-D-mannopyranoside from benzyl (Product 18)

The oxidized compound 15a/15b (180 mg, 0.149 mmol) is solubilised in a dichloromethane/THF mixture (1:1, v/v) and then added to -78 °C L-selectride (1M in THF; 150 μL, 0.150 mmol). After 45 minutes at -78 °C, the reaction is assumed to be complete and neutralized by adding a few drops of acetic acid. Once the medium has returned to room temperature, 30 mL of dichloromethane is added and the organic phase is washed with a 10% aqueous solution of hydrochloric acid, a saturated solution of sodium hydrocarbonate and finally a saturated aqueous phase of sodium chloride. Product 18 : white solid; Pf (°C) 180; Rf (EP/AcOEt, 2:1) 0,2;αD20The following is the list of substances which are to be classified as 'compounds' in the Annex to Regulation (EC) No 1907/2006 of the European Parliament and of the Council of 16 December 2006 on the approximation of the laws of the Member States relating to the permissible sound power level of compressed air:

[h]- Preparation of 4,6-O-benzylidene-3-O-(2-methylnaphthyl) -β-D-glucopyranosyl-(1→3)-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4,6-O-benzylidene-β-D-mannopyranoside from benzyl (Product 19)

Compound 18 (170 mg, 0.141 mmol) is dissolved in 15 mL of a methanol/dichloromethane mixture (2:1, v/v) and then added 2 sodium methyl equivalent (0.1M in MeOH, 3 mL, 0.300 mmol). After 6 hours of stirring at room temperature, the medium is neutralized by addition of Amberlite IR120-H+ resin, filtered and then concentrated under reduced pressure. After chromatography [dichloromethane/methanol (99:1 ; v/v) ], compound 19 is obtained with an efficiency of 72% (126 mg).Products 19 white solid; (°C) > 230 °F; (CH2Cl2 / MeOH, 97 °F; 0.4 °C)αD20The following is a list of the substances which are to be used in the preparation of the product: 1. the active substance, which is to be classified as a substance of a particular kind, and 2. the active substance, which is to be classified as a substance of a particular kind, which is to be classified as a substance of a particular kind, and 3. the active substance, which is to be classified as a substance of a particular kind, which is to be classified as a substance of a particular kind, and 3. the active substance, which is to be classified as a substance of a particular kind, which is to be classified as a substance of a particular kind, and 3. the active substance, which is to be classified as a substance of a particular kind, which is to be classified as a substance of a particular kind, and 3. the active substance, which is to be classified as a substance of a particular kind, which is to be classified as a substance of a particular kind, and 4. the active substance, which is to be classified as a substance of a particular kind, which is to be classified as a substance of a particular kind, and which is to be classified as a substance of a particular kind, and which are to be classified as substances of a specific kind, and which are to be classified as substances of a specific kind, and which are to be classified as substances of a specific kind, and which are to be classified as substances of a specific kind, and which are to be classified as substances of a specific type, and which are to be classified as substances of a specific type, and which are to be classified as substances of a specific type, and which are to be classified as substances of a specific type, and of a specific type, and of a specific, and of a kind, and of which are to which are to be classified as substances of a kind:

[i]- β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-α,β-D-mannopyranose (Product A1)

In 10 mL of a mixture of ethyl/methanol/dichloromethane acetate (2:2:1; v/v/v), trisaccharide 18 (90 mg, 0,090 mmol) and palladium acetate (60 mg, 0,267 mmol) are added, the medium is then vigorously agitated at room temperature under hydrogen atmosphere for 7 days. After filtration on cellite, the hydro-organic phase is extracted to dichloromethane, then is dried by azeotropic co-evaporation with ethanol to lead quantitatively to the desired compound (45 mg, 0,090 mmol). 25 mg of the compound is then formed by defrosting the gel formed by chromatography to remove the white matter: Gluorophil (Gluorophil) and lyophil (Gluorophil) are then obtained in the form of a freshly purified liquid which is then coated with water.- What? The maximum value of the measurement is the value of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurThe frequency range of the measurement is defined as the frequency range of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measurement of the measur

EXAMPLE 2: Synthesis of various intermediates:

2.1/ 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl- (((1→3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranoside of benzyl (Product 8)

2,3-dichloro-5,6-dicyano-1,4-benzoquinone (176 mg, 0,774 mmol) is added to a solution of the trisaccharide compound 7 (337 mg, 0,258 mmol) in a dichloromethane/methanol mixture (4:1 v/v). After 16 hours of agitation at room temperature, the reaction is completed and the medium is diluted with dichloromethane, washed with a saturated solution of sodium hydrocarbonate and then with water. The organic phase is dried to MgSO4, concentrated and the silica product 8 is obtained after purification on a research gel [petroleum ether/ethyl acetate (2:1 v/v) ] (185 mg, R = 72%). The test chemical is a white solid; Rf (EP/AcOEt, 2:1) 0,2.RMN1H (CDCl3, 400 MHz) δ (ppm): 8,The following are the main components of the test method: - the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the pH of the test medium, the measurement of the test medium, the measurement of the test medium, the measurement of the test medium, the measurement of the test medium, the measurement of the test medium, the measurement of the test medium, the measurement of the test medium, the measurement of the test medium, the measurement of the test medium, the measurement of the test medium, the measurement of the test medium, the measurement of the test medium, the test, the measurement of the test method, the measurement of the test medium, the test, the measurement of the test, the measurement of the test, the test, the measurement of the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test,The following are the main components of the product:

2.2/O-benzoyl-4,6-O-benzylidene-3-O-(2-methylnaphthyl) -β-D-glucopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranoside of benzyl (Product 9)

After adding N-iodosuccinimide (NIS) (50mg, 0.051 mmol) and trimethylsilyl triflate (0.65 μL, 0.004 mmol), the mixture is left to agitate for 30 minutes. When the reaction is complete, the medium is neutralized by triethylamine, filtered and then concentrated. After chromatography on silica [toluene/ethylene acetate (2:1 v/v) ], 24 mg of tetrasalcyte 9 9 are obtained; with a desired yield of 34%. Product 9 : white solid; Pf (°C) 138; Rf (EP/AcOEt, 2:1) 0,3; αD20The following is the list of substances which are to be classified as substances of very high concern in accordance with the provisions of Regulation (EC) No 1907/2006 of the European Parliament and of the Council of 16 December 2006 on the approximation of the laws of the Member States relating to the placing of dangerous substances on the market and the placing on the market of dangerous substances:The value of the product obtained from the product is calculated by multiplying the value of the product by the value of the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product obtained from the product.The following are the main components of the test method: - the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the test chemical, the testThe following is the total number of units of measurement of the product, calculated as the sum of the total number of units of measurement of the product, calculated as the sum of the total number of units of measurement of the product, calculated as the sum of the total number of units of measurement of the product, calculated as the sum of the total number of units of measurement of the product, calculated as the sum of the total number of units of measurement of the product, calculated as the sum of the total number of units of measurement of the product, calculated as the sum of the total number of units of measurement of the product, calculated as the sum of the total number of units of measurement of the product, calculated as the sum of the total number of units of measurement of the product, calculated as the sum of the total number of units of measurement of the product, calculated as the sum of the total number of units of measurement of the product, calculated as the sum of the total number of units of measurement of the product, calculated as the sum of the total number of units of measurement of measurement of the product, calculated as the sum of the total number of units of measurement of measurement of the product, calculated as the sum of the sum of units of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measurements of measThe following is the list of the substances which are to be classified as 'metals' in the Annex to Regulation (EC) No 1907/2006 of the European Parliament and of the Council [1]:

2.3/ 4,6-O-benzylidene-3-O-(2-methylnaphthyl) -β-D-glucopyranoside of benzyl (Product 10)

Sodium (0.7 g, 30.435 mmol) is added to a 3 (5 g, 8.296 mmol) solution in anhydrous methanol (150 mL). The mixture is agitated at 50 °C until the starting product is completely consumed. The medium is then cooled, neutralized by addition of a stoichiometric amount of acetic acid and concentrated. The residue is then dissolved in dichloromethane (250 mL), extracted 3 times per 50 mL of water. The organic phase is dried on MgSO4 and then concentrated. Product 10 : white solid; Pf (°C) 148; Rf (EP/AcOEt, 3:1) 0.7;αD20The following is a list of the substances which are to be used in the preparation of the test chemical: 48,1 (c=1,0, CH2Cl2).RMN 1H (CDCl3, 400 MHz) δ (ppm) : 7,96-7,80 (m, 2H, H arom.) ; 7,78-7,72 (m, 1H, H arom.) ; 7,52-7,30 (m, 14H, H arom.); 5,60 (s, 1H, H7) ; 5,10 (d, 1H, H9, JH9-H9' = 12,0 Hz) ; 4,98 (d, 1H, H8, JH8-H8' = 11,8 Hz) ; 4,65 (d, 1H, H8') ; 2,46 (s, 1H, H) ; table 1a.RMN 13H (m, 14H, H arom.) ; 7,52-7,30 (m, 14H, H arom.); 5,60 (s, 1H, H, H arom.); 5,10 (d, 1H, 1H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H) ; 5,10 (d, 1H, 1H, 1H, 1H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H, H) ; 5,104-7,02-7, 7,30 (m, 140, 140, 140, 140, 140, 140, 140, 140, 140, 140, 140, 140, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 150, 15

2.4/2-O-benzoyl-4,6-O-benzylidene-3-O-(2-methylnaphthyl) -β-D-glucopyranosyl-(1→3)-4,6-O-benzylidene-β-D-glucopyranoside of benzyl (Product 11)

200 μL of a 1M solution of hydrazine in a pyridine/acetic acid mixture (3:2, v/v) are added drop by drop to a solution of disaccharide 5 (11 mg, 0,011 mmol) in pyridine (0.2 mL). After 1 hour of agitation, the reaction is stopped by adding 50 μL of 2,4-pentane-dione and the medium is concentrated under reduced pressure. The residue is then picked up by 20 mL of dichloromethane and washed by a 10% solution of hydrochloric acid, by an aqueous solution saturated with sodium hydrogen carbonate and by an aqueous solution saturated with sodium chloride. After drying the organic phase on MgSO4 and evaporation of the solvent, the solution is then washed off with a mixture of the following:The product is purified by silica gel chromatography (petroleum ether/ethyl acetate (2:1; v/v) ] to lead to 6 mg of compound 11 with an efficiency of 61%. Product 10 : white solid; Rf (EP/AcOEt, 2:1) 0.6. The following values are used for the calculation of the mean free path of the measurement:- What? The following is the list of the substances that are to be used in the preparation of the feed additive: The measurement of the measured m/z is based on the following equation:

The following substances are to be classified in the same category as the active substance:

Compound 10 (43.5 mg, 0.087 mmol) is dissolved in 1 mL of a DMSO/acetic anhydride mixture (2:1; v/v). After 20 hours of stirring at room temperature, the medium is taken up by 50 mL of ethyl acetate and washed by a saturated aqueous solution of sodium hydrocarbonate and a saturated aqueous solution of sodium chloride. After drying (MgSO4) and concentration of the organic phase, the compound is purified by silica gel chromatography (3:1; v/v) to yield 33 mg of a mixture of 13 mg of 13a and 5:1 hydrate of 13b compound,with a yield of 76%. White solid; Rf (EP/AcOEt, 3:1) 0.3 The following is a list of the substances which are to be classified as white solids: The following is the list of the most commonly used methods of measuring the frequency of the radio frequency spectrum:The following are the values for the two-phase flow rate: The following are the values of the values of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the The following is a list of the most commonly used methods of measuring the concentration of HCl in the atmosphere:The following are the main components of the test method: H) 5,49 (s, 1H, H7) ; 4,97 (d, 1H, H9, JH9-H9' = 11,9 Hz) ; 4,94 (d, 1H, H9') ; 4,84 (d, 1H, H8, JH8-H8' = 11,7 Hz) ; 4,58 (d, 1H, H8'); 4,38 (s, 1H, H1); 4,28 (dd, 1H, H6, JH5-H6 = 4,8 Hz, JH6-H6' = 10,4 Hz) ; 3,84 (t, 1H, H4, JH3-H4 = JH4-H5 = 9,9 Hz) ; 3,80 (dd, 1H, H6', JH5-H6' = 9,7 Hz) ; 3,62 (d, 1H, H8'); 3,34 (s, 1H, H5) ; 1,95 (s, 1,95), OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, OH, The following is a list of the active substances in the active substance:The following are the headings which are to be considered in the calculation of the adjustment for the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjustment to the adjust

The following shall be indicated in the column for the product:

Compound 11 (6 mg, 0.007 mmol) is dissolved in 1 mL of a DMSO/acetic anhydride mixture (2:1; v/v). After 20 hours of stirring at room temperature, the medium is taken up by 50 mL of ethyl acetate and washed by an aqueous solution saturated with sodium hydrocarbonate and an aqueous solution saturated with sodium chloride. After drying (MgSO4) and concentration of the organic phase, the compound is purified by silica gel chromatography [petroleum ether/ethyl acetate (2:1; v/v) ] to yield 6 grats of a mixture of the compound 1:5 mg 14a and the hydrochloride compound 14b.The Commission has already made a number of proposals. The white solid; Rf (EP/AcOEt, 2:1) 0.3. The following is the list of the most commonly used methods of measuring the pH of the water: the measurement of the pH of the water, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, the measurement of the water content, measurement of the water content, measurement of the measurement of the water content, measurement of the water content, measurement of the water content, measurement of the water content, measurement of the water content of the waterThe following is a list of the substances which are to be classified in the Annex to this Regulation:The following are the headings of the ECB 's monetary policy: (a) the ECB 's monetary policy; (b) the ECB 's monetary policy; (c) the ECB 's monetary policy; (d) the ECB 's monetary policy; (e) the ECB 's monetary policy; (f) the ECB 's monetary policy; (g) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; (h) the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy; the ECB 's monetary policy

2.7/ 4,6-O-benzylidene-3-O-(2-methylnaphthyl) -β-D-mannopyranoside of benzyl (Product 16)

After 15 minutes of agitation at -80 °C, the medium is diluted with 10 mL of dichloromethane and washed with a 10% aqueous solution of hydrochloric acid, a saturated aqueous solution of sodium hydrocarbonate and an aqueous solution of sodium chloride. After drying on MgSO4 and evaporation of the solvent, the test compound is purified by chromatography on silica gel [petroleum ether/acetate of compound (3:1 v/v) ] to produce 28 mg of mannosodium at a conductivity of 16 to 85%.- What? The following is the list of the substances which are to be classified as 'compounds' in the Annex to Regulation (EC) No 1907/2006 of the European Parliament and of the Council:The following are the values of the measurements to be performed for the measurement of the emission of the emission of the measuring medium:

2.8/2-O-benzoyl-4,6-O-benzylidene-3-O-(2-methylnaphthyl) -β-D-glucopyranosyl-(1→3)-4,6-O-benzylidene-β-D-mannpyranoside from benzyl (Product 17)

Compound 14a/14b (5 mg, 0.006 mmol) in solution in 1 mL of THF is added to L-Selectride (solution 1M in THF; 6 μL, 0.006 mmol) at -90 °C. After 1 hour of low temperature agitation, the medium is neutralized with acetic acid, diluted with 20 mL of dichloromethane and washed with 10% aqueous solution of hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride. After drying (MgSO4) and concentration of the organic phase, 5 mg of the desired compound (0.17006 mmol) is obtained with a quantitative saturation.- What? The following is the list of substances which are to be classified as 'compounds' in the Annex to Regulation (EC) No 1907/2006 of the European Parliament and of the Council:The following is the list of substances which are to be classified as 'organic' in the Annex to Regulation (EC) No 1907/2006 of the European Parliament and of the Council:

The following shall be added to the list of active substances:

The desired product was prepared according to a protocol comparable to that described for product A1 by applying to product 9 the successive steps [d], [c], [d], [c], then [e] to [i]. The result is the product A2 which is in the form of a white foam; Rf (AcOEt/iPrOH/H2O, 3:2:2) 0.2. The measurement of the frequency of the measurement shall be performed in accordance with the following equation: Other signals: 1H (D2O, 400 MHz) δ (ppm) : 4,75 (d, 3H, 3H, 3H1, JH1-H2 = 8,0 Hz) ; 4,71 (d, 2H, 2H1, JH1-H2 = 7,8 Hz) ; 3,93-3,81 (m, 8H, H3a, H4a, H6a, H6b, H6c, H6d, H6e, H6f) : 3,80-3,63 (m, 11H, H2a, H3b, H3c, H3d, H3e, H6'a, H6'b, H6'c, H6'd, H6'e, H6'f) ; 3,55 (m, 11H, H2a, H2c, H2d, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6c, H6e, H6c, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H6e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e, H8e

EXAMPLE 4: Preparation of β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -mannitol (product B1) according to reaction scheme 1

The unprotected trisaccharide A1 (25 mg, 0.049 mmol) is added to 10 mL of a methanol/water mixture (4:1; v/v). Sodium borohydride (19 mg, mmol) is added at room temperature and the medium is left to agitate for 10 days. The medium is then neutralized by adding a few drops of acetic acid and then dried by co-evaporation with a methanol/acetic acid mixture (9:1, v/v), then co-evaporation with methanol. After lyophilization, the compound is purified by Sephadex G-10 (water gel) pervaporation chromatography and the lyophilized fractions are recollected to obtain the resulting B1 in the form of a white foam.- What? The following shall be indicated in the table of the Annex to this Regulation: 'RMN 1H (D2O, 400 MHz) δ (ppm) : 4,82 (d, 1H, H1c, JH1c-H2c = 8,0 Hz) ; 4,65 (d, 1H, H1b, JH1b-H2b = 8,1 Hz) ; 4,09-3,90 (m, 7H, H1a, H2a, H3a, H3a, H5a, H5a, H6a, H6b, H6c) ; 3,86-3,66 (m, 6H, H1'a, H4a, H6'a, H3b, H6'b, H6'c) ; 3,64-3,38 (m, 7H, H2b, H4b, H5b, H2c, H3c, H4c, H5c).RMN 13D (O2C, 100 MHz) ; 10b, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7c, 7cThe following are the values of the values of the derivatives of the equations of motion:

Example 5: Preparation of product A1 according to reaction diagram 2.

5.1/ Preparation of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-acetyl-β-D-glucopyranosyl- ((1→3)-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranoside from benzyl (Product 21)

In a balloon, donor 20 [Blattner, R.; Furneaux, R. H.; Pakulski, Z. Carbohydr. Res. 2006, 341, 2115-2125.] (50 mg, 0.064 mmol) and acceptor 4 (27 mg, 0.058 mmol) are introduced into anhydrous dichloromethane at -50 °C, in the presence of molecular sieve 4Å. Trimethylsilyl triphlate (0.53 μL, mmol) is then added and the mixture is vigorously stirred for 2 hours. When the reaction is completed, the medium is neutralized by triethylamine, then filtered.- What? The following is the list of substances which are to be classified as 'compounds' in the Annex to Regulation (EC) No 1907/2006 of the European Parliament and of the Council [1]:The following are the main components of the test method: - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium; - the measurement of the measurement of the test substance in the test medium; - the measurement of the concentration of the test substance in the test medium.The following is the list of substances which are to be classified as chemicals in the feed additive: - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals which are to be classified as chemicals in feed additives, - chemicals in feed additives, - which are to be classified as chemicals in feed additives, - chemicals in feed additives, - which are to be classified as chemicals in feed additives, and which are to be classified as chemicals in feed additives.The following are the main types of securitisation: - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation positions , - securitisation , - securitisation , - securitisation , - securitisation , - securitisation , - securitisation , - securitisation , - securitisation , - securitisation , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis , - securitis ,

5.2/ Preparation of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-acetyl-β-D-glucopyranosyl- ((1→3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl- ((1→3)-4,6-O-benzylidene-2-O-levulinoyl-β-D-glucopyranoside from benzyl (Product 22)

The dissaccharide donor 37 (106 mg, 0.136 mmol) and acceptor 71 (100 mg, 0.123 mmol) are introduced into a balloon in anhydrous dichloromethane at -50 °C, in the presence of a molecular sieve of 4Å. Trimethylsilyl triflate (1,1 μL, 0.006 mmol) is added and the reaction is agitated for 60 minutes. The medium is neutralized by triethylamine, filtered and then concentrated. After purification by silica gel chromatography [petroleum ether/ethyl acetate (1:1 v/v) ], 146 mg of tetrahydrocorthoester tetrahydrocorthoester are obtained with an efficiency of 83%. The compound is thus directly involved in an intramolecular reaction in the presence of trimethyl triflate (2,After 3 hours of agitation, the medium is neutralized by triethylamine and then concentrated. After purification by silica gel chromatography [petroleum ether/ethyl acetate (1:1; v/v) ], 101 mg of the expected product 22 are obtained with an efficiency of 69%. The following is the list of the substances which are to be classified in the product:The following substances are to be classified in the same category as the product: (a) aromatic substances (d, 1H, H8'a); (b) aromatic substances (d, 1H, H8'a); (c) aromatic substances (d, 1H, H8'a); (d, 1H, H8'a); (d, 1H, H8'a); (d, 1H, H8'a); (d, 1H, H8'a); (d, 1H, H8'a); (d, 1H, H8'a); (d, 1H, H8'a); (d, 1H, H8'a); (d, 1H, H8'a); (d, 1H, H8'a); (d, 1H, H8'a); (d, 1H, H8'a); (d, 1H, H8'a); (d, 1H, H8'a); (d, 1H, H8'a); (d, 2H, 1H, H8'a); (d, 2H), 2H, 2H, 2H, H8'a); (d, 2H, 1H, H8'a); (d, 1H, 1H, H8'a); (d, 1H, 1H, H8'a); (d, 2H8'a); (d, 2H), 2H, 2H, 2H, 2H, H8'a; (d, 1H, 1H, H8'a); (d, 1H, 1H, 1H, H8'a); (d, 2H1'a); (d, 2H), 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 2H, 3H, 3H, 3H, 3H, 3H, 3H, 3H, 3The following table is used for the calculation of the mean value of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the measured values of the

5.3/ 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-acetyl-β-D-glucopyranosyl- ((1→3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl- ((1→3)-4,6-O-benzylidene-β-D-glucopyranoside of benzyl (Product 23)

Tetrasuccaride 22 (430 mg, 0.301 mmol) is dissolved in 6 mL of pyridine and then 6 mL of hydrazine 1M solution is added drop by drop into a pyridine/acetic acid mixture (3:2, v/v). After 3 hours of stirring, the reaction is stopped by adding 1.7 mL of 2,4-pentane-dione and concentrated under reduced pressure. The medium is picked up by 50 mL of dichloromethane and washed by a 10% solution of chloric acid, by an aqueous solution saturated with sodium hydrocarbonate and by an aqueous solution saturated with sodium chloride. After drying (MgSO4) and concentration, the product is deprototyped by chromatography of petroleum gels [ethyl silica 1:1; 23 g/v] to produce a 65% efficiency of the hydrated silicate. Product 23 : white solid; Pf (°C) 136; Rf (EP/AcOEt, 1:1) 0.3;αD20The following is the list of substances that are to be classified as chemicals in the feed additive: 1,4-dichloropropanol, 1,4-dichloropropanol, 1,4-dichloropropanol, 1,4-dichloropropanol, 1,4-dichloropropanol, 1,4-dichloropropanol, 1,4-dichloropropanol, 1,4-dichloropropanol, 1,4-dichloropropanol, 1,4-dichloropropanol, 1,4-dichloropropanol, 1,4-dichloropropanol, 1,4-dichloropropanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophanol, 1,4-dichlorophan

5.4/ Preparation of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-acetyl-β-D-glucopyranosyl- ((1→3)-2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl- ((1→3)-4,6-O-benzylidene-β-D-glucopyranos-2-uloside from benzyl (Product 24a) and of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-acetyl-β-D-glucopyranosyl- ((1→3) 2-benzoyl-4,6-O-benzylidene-D-glucopyranosyl-β-benzylidene-β-hydroxy-butadiene-β-butadiene-β- (Product 24a)

After 24 h at room temperature, ethyl ether is added to the medium. The resulting precipitate is filtered on cellite and the concentrated filtered under reduced pressure. The residue is finally purified by silica gel chromatography [petroleum ether/ethyl acetate (1:1; v/v) ] to lead to 208 mg of the oxidized product 24a (Rdt=80%) in the mixed form (1:1) with its hydrated form 24b. 24a/24b: white solid; Rf (EP/AcOEt,The following is a list of the most commonly used methods of measuring the frequency of the radio frequency spectrum: Other signals (24a/24b): The following is the list of the active substances in the active substance:The following equation is used for the calculation of the concentration of the product in the sample: 5,18 (m, 2H, 2H, 2H2b); 5,14-4,80 (m, 14H, H2c, 2H2d, 2H3d, 2H4a, 2H4b, 2H8a, 2H1); 4,73 (d, 1H, H8a, JH8a-H8a = 11,9 Hz); 4,66-4,48 (m, 6H, H3a, H8a, 2H1, H6, H7); 4,42-4,26 (m, 6H, H3a, H1, H7, 3H6); 4,20-3,40 (m, 28H, 2H3b, 2H3c, 2H4c, 2H4d, 2H5a, 2H5b, 2H5c, 2H5c, 2H5d, 2H6a, 2H6b, 2CH6c, 2H6c, 2H6d, 2H6c, 2H6d, 2H6n, 2H6n, 2H6n, 2H6n, 2H6n, 2H6n, 2H6n, 2H6n, 2H6n1, 2H6n, 2H6n1, 2H7, 2H7n1, 2H7n1, 2H70, 2H70, 2H70, 2H70, 2H70, 2H70, 2H80, 2H80, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2H90, 2HThe following are the types of products which may be used: - 1 1 1 2 3 4 5 6 6 6 7 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 9 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 9 8 8 8 9 8 8 9 8 8 9 8 8 9 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 7 8 7 8 7 8 7 8 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 7 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8The following are the main components of the test method:

The following shall be indicated in the column for the product:

The product 24a/24b (66 mg, 0,050 mmol) in solution in a dichloromethane/THF mixture is added to L-Selectride (1 M solution in THF; 150 μL, 0,150 mmol) at -90°C. After 2 hours of low temperature agitation, the medium is neutralized by the addition of acetic acid, diluted with 20 mL of dichloromethane and washed with an aqueous solution saturated with chloric acid, an aqueous solution saturated with sodium hydrocarbonate and water. After drying at SO4 and Mg concentration, the medium is purified by chromatography on silica gel [dichloromethane/thanol (9:28 v/v) ]; the desired product is reduced to 256 mg (650 mmol) with a yield of 0,05%.- What? The following is the list of substances which are to be classified as 'compounds' in the Annex to Regulation (EC) No 1907/2006 of the European Parliament and of the Council:The following substances are to be classified as aromatic substances: aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to be classified as aromatic substances, which are to classified as aromatic substances, which are to classified as aromatic substances, which are to classified as aromatic substances, which are to classified as aromatic substances, which are to classified as aromatic substances, which are to classified as aromatic substances, which are to classified as aromatic substances, which are to classified as aromatic substances, which are to classified as aromatic substances, which are to classified as aromatic substances, which are to classified as aromatic substances, which are to classified as aromatic substancesThe following are the main components of the product, which are to be classified in the same heading as the product:

5.6/ Preparation of product A1

The compound 25 (60 mg, 0.045 mmol) is dissolved in a dichloromethane/methanol mixture (2:1, v/v; 10 mL) and then 2 equivalents of sodium methylate (0.1M in MeOH, 0.9 mL, 0.090 mmol) are added. After 6 hours of stirring at room temperature, the medium is neutralized by adding Amberlite IR120-H+ resin, filtered and then concentrated under reduced pressure. The resulting residue is then dissolved in 10 mL of an ethyl/methanol/dichloromethane acetate mixture (2:2:1 v/v; 10 mL). After adding palladium acetate (60 M in MeOH, 0.9 mL, 0.267 mmol), the medium is heated to absolute strength at room temperature for 7 days. After the final phase of filtration, the medium is dried with a quantitatively dry solution of 30 mg of dichlorothrene (30 mg) and then extracted with a hydroponic isotretine.

Example 6:

Product 1a is obtained as described in patent application FR2804684.

6.1/ Preparation of 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-1,2,4,6-tetra-O-benzoyl- ((α,β) -D-glucopyranose (Product 2a) Other preparations of a kind used as a base for the manufacture of pharmaceutical products

The 1a oligosaccharide (150 mg, 0.181 mmol) is dissolved in 1a pyridine (15 mL). The reaction medium is then cooled to 0 °C and then benzoyl chloride (4.2 mL, 36 mmol) is added. After 2 days of stirring at room temperature, the medium is evaporated, dissolved in dichloromethane and then washed with a 10% aqueous solution of hydrochloric acid, with a saturated solution of sodium hydrogen carbonate and with a saturated solution of sodium chloride until neutral. The organic phase is then dried on MgSO4 and evaporated. The residue is chromatographed on a silica gel [petroleum ether/ethyl ether (3:2; v/benzoyl) ] to give the resulting mixture in the form of 1 1⁄44 μg of α-methanol (4:1; v/benzoyl) to give a yield of 94 μg of α-methanol (4:1).The concentration of the active substance in the blood is 0.170 mmol). The following is the list of characteristic signals for 2a□ 6.65 (d, 1H, H1a, JH1a-H2a=3.6 Hz) ; 5.47 (t, 1H, H4a, JH3a-H4a = JH4a-HSa = 9.4 Hz) ; 4.64 (t, 1H, H3a, JH2a-H3a = 9.4 Hz). Signals characteristic for 2a□ 6.07 (d, 1H, H1a, JH1a-H2a = 7.1 Hz); 5.57 (t, 1H, H4a, JH3a-H4a = JH5a-H; 8.9 (a), 4a, 4a, 4a, 4a, 4a, 7a, 7a, 7a, 7a, 7a, 7a, 7a, 7a, 7a, 7a, 7a, 7a, 7a, 7a, 7a, 7a, 7a, 7a, 7a, 7a, 7b, 7a, 7a, 7a, 7a, 7a, 7b, 7a, 7a, 7a, 7a, 7a, 7a, 7b, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a, 8a,(C5a); 67,6 (C4a). Characteristic signals for 2a□ 89,7 (C1a); 78,4 (C3a); 72,4 (2C, C2a, C5a); 67,6 (C4a); 62,0 (C6a).Other signals: RMN 1H (CDCl3, 400 MHz) δ (ppm) : 8,08-7,92 (m, 68H, H.); 7,61-7,09 (m, 102H, H arom.); 5,45-5,37 (m, 3H, H2aβ, H3e); 5,26-5,18 (m, 5H, H2aα, H2e, H4e); 5,11-4,83 MHz (m, 14H, H1b, H2b, H4b, H2c, H3c, H3d), H4b, H3d, H4c, H4c, H4c, H4c, H4c, H4c, H4c, H4c, H4c, H4c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, H6c, HThe following are the active substances which are to be classified in the active substance: - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance,The following are the main components of the test chemical:

6.2/ Preparation of bromide from 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyrunosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl-→13)-2,4,6-tri-O-benzoyl-α-D-glucopyranosyl (Product 3a)

The perbenzoyl oligosaccharide 2a (444 mg, 0.170 mmol) is dissolved in dichloromethane (10 mL) and then 33% w/w hydrobromic acid is added to acetic acid (0.6 mL, 3.417 mmol) at 0 °C. After 3.5 hours of agitation, the medium is diluted with dichloromethane and then washed with a saturated aqueous solution of sodium hydrocarbonate. The organic phase is then dried on MgSO4 and concentrated at reduced pressure to lead quantitatively to 435 mg of brominated 3a. The following is the list of the characteristic signals of the product:(t, 1H, H4a, JH3a-H4a = 9,9 Hz) ; 4,24 (dd, 1H, H6a, JH5a.H6'a = 4,6 Hz, JH6-H6'a = 12,4 Hz).RMN 13C (CDCl3, 100 MHz) δ (ppm) : Characteristic signals 87,7 (C1a); 76,3 (C3a); 73,4 (C2a); 72,6 (C5a); 67,6 (C4a); 62,0 (C6a).Other signals: RMN 1H (CDCl3, 400 MHz) δ (ppm) : 8,92-7,61 (m, 22H, H.) 7,48 (Hm, 58; 5,27; 5,27; 5,27; 4,3 and 5,86; 4,3 and 4,86; 5,4 and 5,86; 4,3 and 4,4 (Hm, 5,88; 5,4 and 5,84; 5,4 and 5,88; 5,4 and 4,4 (Hm, 5,80); 4,4 and 4,4 (Hm, 9,80); 4,4 and 4,4 (Hm, 5,80); 4,4 and 4,4 (Hm, 9,8 and 4,8 and 4,4 (Hm, 5,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 4,8 and 9, and 4,8 and 4,8 and 4,8 and 9, and 9, and 4,8 and 4,8 and 4,8 and 9, and 4,8 and 4,8 and 9, and 4,8 and 9, respectively, and 4, and 4, and 4,8 and and 4,8 and and and and 4,8 and and and and 4,8 and and and and and 4,8 and and and and and and and 4,8 and and and and and and and and and and and and and and 8, respectively).The following are the active substances which are to be classified in the additive: - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, - the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substance, the active substanceThe following are the main components of the test method:

6.3/ Preparation of 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucupyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1-3)-2,4,6-tri-O-benzoyl-2-D-glu-hex-1-enranopyose (Product 4a) Other preparations of the same name as the active substance

The raw material (3a: 435 mg, 0.170 mmol) is dissolved in dichloromethane (10 mL) and then added 1,8-diazabicyclo[5,4,0]undec-7-ene (40 μL, 0.270 mmol). After 5.5 hours of stirring at room temperature, the medium is diluted with dichloromethane, washed with a 10% aqueous solution of hydrochloric acid, with an aqueous solution saturated with sodium hydrocarbonate, then with an aqueous solution saturated with sodium chloride. The organic phase is dried (MgSO4), dried and the desired product is obtained after purification on silica gel [petroleum ether/ethyl acetate (3:2/v) ]; the composite 4a (343 mg) is then isolated with an isolating yield of 81%.- What? The following is the list of substances which are classified as 'Aromatic' in the Annex to Regulation (EC) No 1907/2006 of the European Parliament and of the Council:The following are the values of the values of the values of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurements of the measurThe following is the list of substances which are to be classified as 'substances' in the Annex to Regulation (EC) No 1907/2006 and which are to be classified as 'compounds' in Annex I to this Regulation:The following are the main components of the test method:

6.5/ Preparation of bromide of 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-4,6-di-O-benzoyl-α-D-glucopyranos-2-ulosyl (Product 5a) Other products of the same heading as the product

The previously described compound 5a (48 mg, 0.019 mmol) in solution in dichloromethane (0.5 mL) is added methanol (1.6 μL, 0.040 mmol). After 10 minutes of stirring at room temperature, N-bromosuccinimide (10.8 mg, 0.060 mmol) is added at 0 °C. Once the reaction is completed, the medium is diluted with dichloromethane and then washed with an ice-saturated aqueous solution of sodium thiosulfate and with ice water. The organic phase is dried on MgSO4 and then concentrated to lead to 5a at reduced pressure with a quantitative yield (47 mg, 0.019 mmol). Product 5a: colourless oil.RMN 1H (CDCl3,The following is the list of the characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signalThe following are the main components of the test method: J2b-H3b = 9,3 Hz; 5,06 - 4,98 (m, 4H, H1b, H4b, H4c, H2d); 4,89 (t, 1H, H4d, JH3d-H4d = JH4d-H5d = 9,5 Hz); 4,88 (dd, 1H, H2c, JH1c-H2c = 7,7 Hz; JH2e-H3e = 8,6 Hz); 4,74 (d, 1H, H1c, JH1c-H2c = 8,2 Hz); 4,69 (d, 1H, H1e); 4,66 - 4,55 (m, 3H, H5a, H6a, H1d); 4,39 - 4,26 (m, 2H, H3b, H3d); 4,24 (m, H3, 4), 10 - 4,24 (m, H3, 3), 3 , 4 , 4 ; 4,86 (m, H3, 4), 84, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 85, 95, 95, 95, 104, 104, 104, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165, 165,The following are the main components of the test method: - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical, - the test chemical - the test chemical, the test chemical, - the test chemical - test chemical, the test chemical - the test chemical - test chemical - the test chemical - test chemical - the test chemical - test chemical - the test chemical - test chemical - test chemical - the test chemical - test chemical - test chemical - the test chemical - test chemical - test chemical - test chemical - the test chemical - test chemical - test chemical - test chemical - test chemical - the test chemical -

6.6/ Preparation of 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-giucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-6-O-benzoyl-4-deoxy-β-D-gluco-hex-3-enopyranosulos-2-ide from benzyl (Product 6a) Mode of operation 1

Benzyl alcohol (7 μL, 0.068 mmol) and 5a (82 mg, 0.034 mmol) ulosyl bromide are dissolved in dichloromethane (1.5 mL) in the presence of a molecular sieve. After 5 minutes of vigorous agitation, triphenylphosphine oxide (19 mg, 0.068 mmol) is rapidly added to the mixture. After 4 days of agitation at room temperature, the medium is filtered on cellite and concentrated under reduced pressure. The target product 6a (69 mg; 0.029 mmol) is obtained after purification on silica gel [petroleum ether/ethyl acetate (3:2 v/v) ] with an 85% yield in hydrated form. The following is the list of the characteristics of the product: 6a: colourless oil; Rf (EP/AcOEt, 1:1) 0,5.RMN 1H (CDCl3, 400 MHz) δ (ppm): characteristic signals 6,26 (d, 1H, H4a, JH4a-H5a = 3,6 Hz); 4,87 (s, 1H, H1a); 4,83 (d, 1H, H7a, JH7a-H7'a = 11,7 Hz); 4,68-4,61 (m, 1H, H5a); 4,60 (d, 1H, H7'a).RMN 13C (CDCl3, 100 MHz) δ (ppm): characteristic signals 183,5 (C2a); 144,9 (C3a); 126,2 (C4a); 97,7 (C1a); 71,5 (C6a); 70,6 (C6a); 66,0 (C6a).

Mode of operation two:

Silver triflate (5,2 mg, 0,020 mmol) is added to a solution of donor 5a (50 mg, 0,020 mmol) and benzyl alcohol (4.4 μL, 0,040 mmol) in dichloromethane (0.75 mL) at 0 °C. After 3 hours of agitation, the reaction medium is neutralized by addition of triethylamine, the silver salts are filtered on cellite and the filtrate is concentrated under vacuum. The signal is then transmitted to the receiver.The following substances are to be classified as 'chemicals' in the Annex to this Regulation: - chemicals which are to be classified as 'chemicals' in accordance with the provisions of this Annex; - chemicals which are to be classified as 'chemicals' in accordance with the provisions of this Annex; - chemicals which are to be classified as 'chemicals' in accordance with the provisions of this Annex; - chemicals which are to be classified as 'chemicals' in accordance with the provisions of this Annex; - chemicals which are to be classified as 'chemicals' in accordance with the provisions of this Annex; - chemicals which are to be classified as 'chemicals' in accordance with the provisions of this Annex; - chemicals which are to be classified as 'chemicals' in accordance with the provisions of this Annex; - chemicals which are to be classified as 'chemicals' in accordance with the provisions of this Annex; - chemicals which are to be classified as 'chemicals' in accordance with the provisions of this Annex; - chemicals which are to be classified as 'chemicals' in accordance with the provisions of this Annex; - chemicals which are to be classified as 'chemicals' in accordance with the provisions of this Annex; - chemicals which are to be classified as 'chemicals' in accordance with the provisions of this Annex; - chemicals which are to be classified as 'chemicals' in accordance with the provisions of this Annex; - chemicals which are to be classified as chemicals which are to be classified as chemicals in accordance with the Annex; - chemicals which are to be classified as chemicals which are to be classified as chemicals in accordance with the Annex; - chemicals which are to which are to be classified as chemicals which are to which the same category 'chemicals' in accordance with the same category 'chemicals' in accordance with the same category 'chemicals' in which they are to which they are classified as chemicals'.The following are the elements of the list of substances which are to be classified in the Annex to this Regulation:

m/z théorique: 2377,6522

m/z mesurée: 2377,6516

6.7/ Preparation of 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-6-O-benzoyl-4-deoxy-β-D-mano-hex-3-enopyranosyl from benzyl (Product 7a)

After 90 minutes at -78 °C, the reaction is assumed to be complete and neutralized by the addition of a few drops of acetic acid. Once the medium has reached room temperature, dichloromethane is added and the organic phase is washed with a 10% aqueous solution of hydrochloric acid, an aqueous solution saturated with sodium hydrocarbonate and an organic solution saturated with sodium chloride. The desired composition is obtained after drying (SOMg4) and the organic phase concentration is 0.8 mg;029 mmol; 100%). The following is the list of the characteristics of the aromatic characteristics of the product: Rf (EP/AcOEt, 1:1) 0,5.RMN 1H (CDCl3, 500 MHz) δ (ppm): characteristic signals 4,94 (d, 1H, H4a, JH4a-H5a = 1,1 Hz); 4,86 (d, 1H, H7a, JH7a-H7'a = 12,0 Hz); 4,59 (d, 1H, H7'a); 4,44 (d, 1H, H1a, JH1a-H2a = 2,2); 4,25-4,20 (m, 2H, H5a, H6a).RMN 13C (CDCl3, 100 MHz) δ (ppm) characteristic signals 151,4 (C3a); 104,1 (a); 97,1 (C7a); 57,1 (a); 70,1 (a), 67,1 (a), 67,1 (a), 67,1 (a), 77,1 (c), 70,1 (a), 67,1 (a), 67,1 (b), 67,1 (c), (c), (d), (c), (d), (d), (d), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (e), (The following are the main components of the test method: • the test chemical, which is a chemical compound with a high molecular weight, and the test chemical, which is a chemical compound with a low molecular weight. • the test chemical, which is a chemical compound with a low molecular weight, which is a chemical compound with a low molecular weight. • the test chemical, which is a chemical compound with a high molecular weight. • the test chemical, which is a chemical compound with a low molecular weight. • the test chemical, which is a chemical compound with a high molecular weight. • the test chemical, which is a chemical compound with a low molecular weight. • the test chemical, which is a chemical compound with a high molecular weight. • the test chemical, which is a chemical compound with a high molecular weight. • the test chemical, which is a chemical compound with a low molecular weight. • the test chemical, which is a chemical compound with a high molecular weight. • the test chemical, which is a chemical compound with a low molecular weight. • the test chemical, which is a chemical compound with a high molecular weight. • the test chemical, which is a chemical compound with a high molecular weight. • the test chemical, which is a chemical compound with a high molecular weight. • the test chemical, which is a chemical compound with a high molecular weight. • the test chemical, which is a chemical, which is a chemical compound with a high molecular weight. • the test chemical, which is a chemical, which is a chemical, which is a chemical, which is a chemical, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, which is, is, which is, which is, which is, which is, which is, which is, is, which isThe following are the main components of the test method: (i) the measurement of the concentration of the active substance in the test chemical, (ii) the measurement of the concentration of the active substance in the test chemical, (iii) the measurement of the concentration of the active substance in the test chemical, (iv) the measurement of the concentration of the active substance in the test chemical, (v) the measurement of the concentration of the active substance in the test chemical, (v) the measurement of the concentration of the active substance in the test chemical, (v) the measurement of the concentration of the active substance in the test chemical, (v) the measurement of the concentration of the active substance in the test chemical, (v) the measurement of the concentration of the active substance in the test chemical, (v) the measurement of the concentration of the active substance in the test chemical, (v) the measurement of the concentration of the active substance in the test chemical, (v) the measurement of the concentration of the active substance in the test chemical, (v) the measurement of the concentration of the active substance in the test chemical, (v) the measurement of the concentration of the active substance in the test chemical, (v) the measurement of the concentration of the active substance in the test chemical, (v) the measurement of the concentration of the active substance in the test chemical, (v) the measurement of the concentration of the active substance in the test chemical, (v) the measurement of the concentration in the test chemical, (v) the measurement of the concentration in the test chemical, (v) and the measurement of the measurement of the concentration in the test chemical, (v) and the measurement in the test chemical, (v) and the measurement in the test chemical, the test, the measurement in the test, the test, the test, the measurement, the measurement, the measurement, the measurement, the measurement, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test, the test,

m/z théorique: 2379,6678

m/z mesurée: 2379,6667

m/z théorique: 2395,6418

m/z mesurée: 2395,6542

6.8/ Preparation of β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-deoxy-β-D-mano-hex-3-enopyranosyl of benzyl (Product 8a)

After 6 hours of agitation at room temperature, the medium is neutralized by addition of Amberlite IR120-H+ resin, filtered and then concentrated under reduced pressure. The debenzoyl compound 8a is obtained after chromatography [dichloromethane/methane (99:1; v/v) ] with a quantitative yield (25 mg; 0,028 mmol). The following is the list of the characteristics of the product:The following is the list of the characteristics of the signal: characteristic signals 153,5 (C3a); 103,8 (C4a); 99,8 (C1a); 71,2 (C7a); 67,2 (C2a); 65,6 (C6a).Other signals: characteristic signals 1H (H), 400 MHz (d), 7,35-7,16 Hz; 7,35-7,16 Hz; 4,71 (d), 4,71 (d), 4,71 (b), 4,1 (d), 3,1 (e), 4,1 (e), 4,1 (e), 4,1 (e), 7,2), 4,8 (e), 7,5 (e), 4,1 (e), 4,1 (e), 7,2), 4,1 (e), 4,1 (e), 7,2), 4,1 (e), 4,1 (e), 4,1 (e), 7,2), 4,1 (e), 4,1 (e), 4,1 (e), 7,2), 4,1 (e), 4,1 (e), 7,2 (e), 4,1 (e), 4,1 (e), 5,1 (e), 7,2 (e), 4,1 (e), 4,1 (e), 5,1 (e), 5,1 (e), 5,1 (e), 5,1 (e), 1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,1,2,1,2,1,2,1,2,1,2,1,2,1,2,1,2,1,2,1,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,2,The following is the list of substances which are to be classified in the additive: acids, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides, peroxides peroxides, peroxides peroxides, peroxides peroxides, peroxides peroxides peroxides, peroxides peroxides peroxides peroxides peroxides peroxides peroxides peroxides peroxides peroxides peroxides peroxides peroxides peroxides peroxides peroxides peroxides peroxidesThe following are the main components of the test method:

6.9/ Preparation of β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-deoxy- ((α,β) -D-mannopyranose (Product Ca)

After dissolving compound 8a (24 mg, 0.027 mmol) in methanol, palladium acetate (25 mg, 0.111 mmol) is added to the medium. After 7 days of agitation under a hydrogen atmosphere at room temperature, the medium is filtered and then concentrated under reduced pressure. The following is a list of the characteristics of the signal: Ca: white foam; Rf (AcOEt/iPrOH/H2O, 3:2:2) 0.2.RMN 1H (D2O, 400 MHz) δ (ppm): characteristic signals 5,12 (m, 1H, H1aα) ; 1,72-1,60 (m, 2H, H4a, H4'a).RMN 13C (D2O, 100 MHz) δ (ppm): characteristic signals 96,(C1a) 67,2 (C2a) ; 61,0 (C6a) ; 28,8 (C4a).Other signals: RMN 1H (D2O, 400 MHz) δ (ppm) : 4,68 (d, 2H, 2 H1, JH1-H2 = 8,2 Hz) ; 4,64 (d, 2H, 2 H1, JH1-H2 = 8,0 Hz); 3,86-3,73 (m, 5H, H6a, H6b, H6c, H6d, H6e); 3,71-3,56 (m, 10H, H2a, H5a, H6'a, H3b, H6'b, H3c, H6'c, H3d, H6'd, H6'e) 3,55m-3,33 (d, 2H, 2H, 2H3a, J3b, H3b, H3b, H3c, H3c, H4d, H4d, H4d, H4e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, H5e, HThe frequency range of the FMC is defined as the frequency range of the FMC of the Member State of transmission, which is the frequency of the FMC of the Member State of transmission.

m/z théorique: 835,2695

m/z mesurée: 835,2694

Example 7:

Product 1b is prepared in the manner described in patent application FR2804684, in the manner described in example 6.

7.1/ Preparation of 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-1,2,4,6-tetra-O-benzoyl-(α,β) D-copyranose (Product 2b)

The reaction medium is then cooled to 0 °C and then benzoyl chloride (5.2 mL, 44.4 mmol) is added. After 2 days of stirring at room temperature, the medium is evaporated, dissolved in dichloromethane and then washed with a 10% aqueous solution of hydrochloric acid, a saturated solution of sodium hydrocarbonate and a saturated solution of sodium chloride until neutral. The organic phase is then dried on MgSO4 and evaporated. The residue is chromatographed on silica gel [petroleum ether/ethyl acetate v:1; 1/b] to give the resulting solution in the form of a 2 mg/a puree (5:1/145 μg, 85% α-methanol).The total volume of the test chemical is 0.178 mmol). The following is the list of the characteristics of the two types of signal: characteristics for 2bββ 6,02 (d, 1H, H1a, JH1a-H2a = 7,1 Hz) characteristics for 2bβ 6,02 (d, 1H, H1a, JH1a-H2a = 7,1 Hz) characteristics for 2bβ 6,02 (d, 1H, H1a, JH1a-H2a = 7,1 Hz) characteristics for 2bβ 6,02 (d, 1H, H1a, JH1a-H2a = 7,1 Hz) characteristics for 2bβ 6,02 (d, 1H, H1a, JH1a-H2a = 7,1 Hz) characteristics for 2bβ 6,02 (d, 1H, H1a, JH1a-H2a = 7,1 Hz) characteristics for 2bβ 6,02 (d, 1H, H4a, JH3a-H4a = JH4a-H5a = 9,0 Hz) characteristics for 2bβ 78, 7bbbbb (a), 7b (a), 7b (a), 7b (a), 7b (a), 7b (a), 7b (a), 7b (a), 7b (a), 7b (a), 7b (a), 7b (a), 7b (a), 7b (a), 7b (a), 7b (a), 7b (a), 7b (a) (a) (b) (a) (b) (b) (b) (b) (b) (c) (c) (c) (d) (d) (c) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d) (d)(C1a) 78,3 (C3a) ; 72,9 (C5a) ; 72,5 (C2a) ; 68,8 (C4a) ; 62,7 (C6a).Other signals: 1H RNA (CDCl3, 400 MHz) δ (ppm) 8,01-7,65 (m, 60H, H arom.) ; 7,55-7,01 (m, 140H, H arom.) ; 5,36-5,30 (m, 3H, H2aβ, H3f) ; 5,20-5,12 (m, 5H, H2aα, H2f, H4f) ; 5,07-4,89 (m, 8H, H2b, 2 H H4) ; 4,88-4,72 (m, 10H, H1b, 2 H2, 2 H4) ; 4,61-4,630 (m, 13d); H3a, H3a, H3a, H3a, H3a, H3a, H3a, H3a, H3a, H3a, H3a, H3a, H3a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6a, H6aThe following is the list of substances which are to be classified in the additive: acids, peroxides, peroxides, peroxides, peroxides, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids, peroxyacids peroxyacids, peroxyacids peroxyacids, peroxyacids peroxyacids, peroxyacids peroxyacids, peroxyacids peroxyacids peroxyacids, peroxyacids peroxyacids peroxyacids, peroxyacids peroxyacids peroxyacids, peroxyacids peroxyacids peroxyacids peroxyacids peroxyacids, peroxyacids peroxyacids peroxyacids peroxyacids peroxyacids peroxyacids peroThe following are the main components of the test chemical:

m/z théorique: 3093,8416

m/z mesurée: 3093,8418

m/z théorique: 3109,8155

m/z mesurée: 3109,8119

7.2/ Preparation of bromide of 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6,-tri-O-benzoyl-α-D-glucopyranosyl (Product 3b)

Bromination of compound 2b (643 mg, 0,209 mmol) is carried out as described for 3a in dichloromethane (15 mL) in the presence of hydrobromic acid (1,1 mL, 6,364 mmol) to give quantitatively 633 mg of brominated compound 3b. The following is the list of the characteristics of the product: colorless oil.RMN 1H (CDCl3, 400 MHz) δ (ppm): characteristic signals 6,68 (d, 1H, H1a, JH1a-H2a = 3,8 Hz); 5,48 (t, 1H, H4a, JH3a-H4a = JH4a-H5a = 9,7 Hz); 4,82 (dd, 1H, H2a, JH2a-H3a = 9,7 Hz); 4,61 (t, 1H, H3a) ; 4,60 (dd, 1H, H6a, JH5a-H6a = 3,8 Hz; JH6a-H6'a = 12,2 Hz) 4,55-4,51 (m,The following is the list of the main characteristics of the HC1a signal: characteristic signals 87,7 (C1a); 76,3 (C3a) 73,4 (C2a); 72,7 (C5a) 67,6 (C4a) 62,0 (C6a).Other signals: RHMN 1H (CDCl3, 400 MHz) δ (ppm) : 8,00-7,71 (m, 26H, H arom.); 7,61-7,03 (m, 69H, H arom.) 5,39 (t, 1H, H3f, JH2f-H3f; JH3f-H3f = 9,7 Hz); 5,22 (m, 1, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4f, H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , HThe following are the main components of the test method: • the measurement of the radiation emitted by the airborne particles (e.g. the airborne particles) and the measurement of the radiation emitted by the airborne particles (e.g. the airborne particles)The value of all the materials of Chapter 9 used does not exceed 20% of the ex-works price of the product and the value of all the materials of Chapter 9 used does not exceed 20% of the ex-works price of the product

7.3/ Preparation of 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-2-D-glucopyranosyl-hex-1-enopyranose (Product 4b)

Compound 3b (550 mg, 0,181 mmol) is engaged in an elimination reaction in the same manner as described for 4a in dichloromethane (10 mL) in the presence of DBU (35 μL, 0,235 mmol). 4b: white solid; Rf (EP/AcOEt, 1:1) 0.5.RMN 1H (CDCl3, 400 MHz) δ (ppm): Signals characteristically 6,54 (s, 1H, H1a) 5,69 (d, 1H, H3a, JH3a-H4a = 1,6 Hz) ; 4,64 (dd, 1H, H6a, JH5a-H6a = 8,The following is the list of the main characteristics of the signal: 138,2 (C1a) ; 74,1 (C5a) ; 72,3 (C4a) ; 68,6 (C3a) ; 61,6 (C6a).Other signals: 1H (C3a) ; 4H (C2a) ; 4H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 5H (C2a) ; 6H (C2a) ; 6H (C2a) ; 6H (C2a) ; 6H (C2a) ; 6H (C2a) ; 6H (C2a) ; 6H (C2a) ; 6H (C2a) ; 6H (C2a) ; 6H (C2a) ; 6H (C2a) ; 6H (C2a) ; 6H (C2a) ; 6H (C2a) ; 7H (C2a) ; 7H (C2a) ; 8H (C2a) ; 8H (C2a) ; 8H (C2H) ; 8H (C2H) ; 8H (C2H) ; 8H (C2H) ; 8H (C2H) ; 8H) ; 8H (C2H) ; 8H (C2H) ; 8H; 8H; 8H; 8H; 8H; 8H; 8H; 8H; 8H; 8H; 8H; 8H; 8H; 8H; 8H; 8H; 8H; 8H; 8H; 8HThe following is a list of the main components of the system: 78-4,71 (m, 3H, H2, 2 H4) ; 4,60 (d, 1H, H1, JH1-H2 = 8,0 Hz) ; 4,52-4,44 (m, 3H, H4a, H5a, H1) ; 4,42-4,35 (m, 3H, 2 H1, H6, JH1-H2 = 8,0 Hz) ; 4,07-4,01 (m, 1H, H5b) ; 3,98 (dd, 1H, H6, JH5-H6 = 3,5 Hz, JH6-H6' = 11,9 Hz) ; 3,93-3,75 (m, 1H, 3 H3c, 8 H6) ; 3,74-3,55 (m, 4H, H5c, H5d, H5e, H5f).RMN 13 (CCl3, 100 MHz) (ppm) : 165, 165, 167, 165, 165, 166, 167, 167, 169, 169, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 129, 139, 129, 129, 129, 129, 139, 129, 129, 139, 129, 129, 139, 129, 139, 169, 132, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 132, 169, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 132, 169, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 139, 13The value of all the materials of Chapter 9 used does not exceed 20% of the ex-works price of the product and the value of all the materials of Chapter 9 used do not exceed 20% of the ex-works price of the product

m/z théorique: 2971,8048

m/z mesurée: 2971,8034

m/z théorique: 2987,7787

m/z mesurée: 2987,7811

7.4/ Preparation of bromide of 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-4,6-di-O-benzoyl-α-D-glucopyranosyl-2-gluulos (Product 5b)

Compound 5b was obtained in the same manner as described for the preparation of 5a from 4b (124 mg, 0,042 mmol) in 1,5 mL dichloromethane, NBS (22,4 mg, 0,126 mmol) and methanol (3,4 μL, 0,084 mmol) with a quantitative yield (123 mg, 0,042 mmol). The following is the list of the characteristic signals of the product: 5b: colourless oil.RMN 1H (CDCl3, 400 MHz) δ (ppm): characteristic signals 6,25 (s, 1H, H1a); 5,44 (t, 1H, H4a, JH3a-H4a = JH4a-N5a = 10,2 Hz); 5,16 (d, 1H, H3a).RMN 13C (CDCl3, 100 MHz) δ (ppm): 1 characteristic signals 91,5 (C2a) ; 83,9 (C1a) ; 76,(C3a) 72,6 (C5a) ; 69,0 (C4a) ; 61,7 (C6a).Other signals: NMR 1H (CDCl3, 400 MHz) δ (ppm): 8,09-7,70 (m, 25H, H arom.) ; 7,60-6,84 (m, 65H, H arom.) ; 5,37 (t, 1H, H3f, JH2f-H3f = JH3f-H4f = 9,7 Hz) ; 5,20 (dd, 1H, H2f, JH1f-H2f = 8,0 Hz) ; 5,19 (t, 1H, H4f, JH4f-H5f = 9,7 Hz) ; 5,10 (dd, 1H, H2b, JH1b-H2b = 8,1 Hz, JH2b-H3b; 9,1 Hz, H2b-H3b; 4,2 Hz, 4,2 Hz, 4,2 Hz, 4,2 Hz, H2b-H3b; 4,2 Hz, 4,2 Hz, H2b-H3b; 4,2 Hz, H2b-H3b; 4,2 Hz, H2b-H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 , H4 ,The following are the main components of the test method: the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, the test method, test method, test method, test method, test method, test method, test method, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, test, testThe total number of samples of the test chemical is calculated by adding the number of samples of the test chemical to the total number of samples of the test chemical.The following are the main components of the test method:

7.5/ Preparation of 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-copyranosyl- ((1→3)-6-O-benzoyl-4-deoxy-β-D-gluco-hex-3-enopyranosuloside-2- of benzyl (product 6b)

Benzyl alcohol (7 μL, 0.068 mmol) and Ulosyl bromide 5b (183 mg, 0.063 mmol) are dissolved in dichloromethane (1.5 mL) in the presence of a molecular sieve. After 5 minutes of vigorous agitation, triphenylphosphine oxide (19 mg, 0.068 mmol) is rapidly added to the mixture. After 4 days of agitation at room temperature, the medium is filtered on cellite, concentrated under reduced pressure and purified by silica chromatography [petroleum ether/ethyl acetate (3:2 v/v) ]. After evaporation of the solvents, the crude obtained is dissolved in benzene (8 mL), water (200,11 μL) and sodium hydrocarbonate (200 mg mol) are added.The medium is then heated to 80°C for 1.5 hours. After return to room temperature, the suspension is dried to MgSO4, filtered and vacuum-concentrated to yield product 6b (120 mg; 0.029 mmol) with an overall yield of 67%. The following is the list of the characteristics of the product: 6b: colourless oil; Rf (EP/AcOEt, 1:1) 0,5.RMN 1H (CDCl3, 400 MHz) δ (ppm): characteristic signals 6,26 (d, 1H, H4a, JH4a-H5a = 3,5 Hz); 4,87 (s, 1H, H1a); 4,83 (d, 1H, H7a, JH7a-H7'a = 11,7 Hz) ; 4,71-4,65 (m, 1H, H5a) ; 4,60 (d, 1H, H7'a).RMN 13C (CDCl3, 100 MHz) δ (ppm): characteristic signals 183,(C2a) 144.9 (C3a) ; 126.3 (C4a) ; 97.7 (C1a) ; 71.0 (C5a) ; 70.6 (C7a) ; 66.1 (C6a).Other signals: NMR 1H (CDCl3, 400 MHz) δ (ppm) : 8.06-7.71 (m, 25H, H arom.) ; 7.60-7.12 (m, 65H, H arom.) ; 5.37 (t, 1H, H3f, JH2f-H3f = JH3f-H4f = 9.5 Hz) ; 5.30-5.16 (m, 5H, H1b, H2b, H2f, H4b, H4f) 5,07-4.94 (m, 6H, H2c, H2d, H2d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4d, H4The following is the list of substances which are to be classified in the additive: - in the form of a mixture of hydrocarbons, containing by weight:The amount of the adjustment to the relevant risk-free interest rate term structure shall be reported in column 060 of line item 'Other financial assets' of line item 'Other financial assets'.

m/z théorique: 2851,7837

m/z mesurée: 2852,7830

m/z théorique: 2867,7576

m/z mesurée: 2867,7508

7.6/ Preparation of 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-glucopyranosyl- ((1→3)-2,4,6-tri-O-benzoyl-β-D-copyranosyl- ((1→3)-6-O-benzoyl-4-deoxy-β-D-manno-hex-3-enopyranosyl from benzyl (Product 7b)

Reduction of compound 6b (104 mg, 0.036 mmol) is carried out in the same manner as described for 7a in the presence of L-Selectride (1M solution in THF; 50 μL, 0.050 mmol) in THF (1 mL). The following are the characteristics of the product: 7b: colourless oil; Rf (EP/AcOEt, 1: 1) 0,5.RMN 1H (CDCl3, 400 MHz) δ (ppm): characteristic signals 4,96 (d, 1H, H4a, JH4a-H5a < 1,0 Hz); 4,60 (d, 1H, H7'a, JH7a-H7'a = 11,7 Hz); 4,45 (d, 1H, H1a, JH1a-H2a = 2,2 Hz);The following are the characteristics of the signal: characteristic signals 151,4 (C3a) ; 104,1 (C4a) ; 97,0 (C1a) ; 70,3 (C5a) ; 70,0 (C7a) ; 66,2 (C6a) ; 65,1 (C2a).Other signals: characteristic signals 13C (CDCl3, 100 MHz) δ (ppm): 8,04-7,73 (m, 25H, H.) ; 7,60-7,10 (m, 65H, H.) ; 5,39 (t, 1H, H3f, JH2f-H3f = JH3f-H4f = 9,7 Hz) 5,34 (t, 1Hb, H4b, H4b, H4b, JH4b, JH4b, JH4f, JH4f, JH4f, JH4f, JH4b, JH4f, JH4f, JH4f, JH4f, JH4b, JH4f, JH4f, JH4b, JH4f, JH4b, JH4f, JH4b, JH4f, JH4b, JH4b, JH4f, JH5b, JH4b, JH4b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JH5b, JThe following is a list of the substances which are to be classified in the Annex to Regulation (EC) No 1907/2006 as additives to the active substance:The following shall be indicated in the column 'C' of the table: 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'C' for the product 'The following are the main components of the test method:

m/z théorique: 2853,7993

m/z mesurée: 2853,7994

m/z théorique: 2869,7732

m/z mesurée: 2869,7650

7.7/ Preparation of β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1-3) -β-D-glucopyranosyl- ((1→3) -4-deoxy-β-D-mano-hex-3-enopyranosyl of benzyl (Product 8b)

Compound 7b (105 mg, 0,036 mmol) is engaged in a debenzoylation reaction in the same manner as described for 8a in a dichloromethane/methanol mixture (3:2 v/v) (2.5 mL) in the presence of MeONa (solution at 0,1 M in MeOH; 0.71 mL, 0.71 mmol). The following is the list of the characteristics of the product:(d, 1H, H7'a) ; 4,49 (d, 1H, H1a, JH1a-H2a = 1,8 Hz) ; 4,12-4,08 (m, 1H, H5a) ; 3,88 (d, 1H, H2a).RMN 13C (CD3OD, 100 MHz) δ (ppm) : Characteristic signals 153,5 (C3a) ; 103,9 (C4a) 99,8 (C1a) ; 71,2 (C7a) ; 67,2 (C2a) ; 65,6 (C6a).Other signals:RMN 1H (CD3OD, 400 MHz) δ (ppm) : 7,30-7,17 (m, 5H, H.) 4,71 (d, 1H, H1b, H1b, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c; 7,7b, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c; 3,8d, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1c, H1The following is the list of the active substances in the feed additive and the total feed additive content of the active substance:The number of cells in the sample shall be calculated as follows:

7.8/ Preparation of β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-deoxy- ((α,β) -D-mannopyranose (Product Cb)

Compound 8b (60 mg, 0,056 mmol) is reduced and debenzyled in the same manner as described for Ca, namely by hydrogenolysis in the presence of palladium acetate (60 mg, 0,267 mmol). The following is the list of the characteristic signals of the product:(C4a).Other signals: 1H RMN (D2O, 400 MHz) δ (ppm) : 4,70 (d, 3H, H1, JH1-H2 = 8,0 Hz) ; 4,66 (d, 2H, H1, JH1-H2 = 8,2 Hz) ; 3,86-3,78 (m, 6H, H6a, H6b, H6c, H6d, H6e, H6f) ; 3,73-3,60 (m, 11H, H3a, H3b, H3c, H3d, H3e, H6a, H6b, H6c, H6d, H6e, H6f) ; 3,50 Hz (d, 16H, H2a, H2b, H2c, H2d; H3e, H3b, H6d, H6d, H6f; H3f, H4f, H4f, H4f, H4f, H4f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H6f, H5f, H5f, H5f, H5f, H6f, H5f, H5f, H5f, H6f, H5f, H5f, H5f, H6f, H5f, H5f, H5f, H6f, H5f, H5f, H5f, H5f, H6f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H6f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, H5f, HThe following are the main categories of products: - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the chemical industry, - products of the manufacture, - products of the chemical industry, - products of the - products of the manufacture, - products of the manufacture, - products of the manufacture, - of the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product, the - product,

m/z théorique: 997,3224

m/z mesurée: 997,3201

Preparation of β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-D-glucopyranosyl- ((1→3) -β-deoxy-D-mannitol (Product Db)

The compound Cb (40 mg, 0.041 mmol) is dissolved in a methanol/water mixture (4:1, v/v) and then added 10 equivalents of sodium borohydride (15.5 mg, 0.411 mmol). After a week of stirring at room temperature, the medium is neutralized by adding a few drops of acetic acid, concentrated under reduced pressure, co-evaporated 3 times with 10 mL of a methanol/acetic acid mixture (9:1, v/v) and finally with 3 times 10 mL of methanol. Product Db: white foam.The following is the list of the characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signal: characteristics of the signalThe following is the list of the substances which are to be used in the preparation of the product: (i) the active substance, (ii) the active substance, (iii) the active substance, (iv) the active substance, (v) the active substance, (v) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi) the active substance, (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi), (vi),

m/z théorique: 999,3380

m/z mesurée: 999,3411

- What? Examples 8 to 11 show the biological activities of compounds of the invention. LAM5 is a laminar-pentaose,LAM7 is a laminar-heptase, A2 is the compound prepared as in Example 3, A0 is the following compound: - What? The witness used is the PBS. The dosages used are 100 μg/ mouse.

EXAMPLE 8: Effect of LAM5, LAM7, A2 and A0 on phagocytosis of peripheral blood cells:

In a group of Balb/c mice (Jackson laboratory, Bar Harbor, ME, USA) one or both of a control, LAM5, LAM7, A0 or A2, was injected peritoneally. 24 hours after the injection the mice were killed. Peripheral blood from the orbital plexus was collected in heparin (5 IU/ml) (Sigma).

After counting, a HEMA particle phagocytosis assay (synthetic microspheres prepared from 2-hydroxyethyl methacrylate copolymer) was performed as described in: Rembaum et al. 1976, Vetvicka et al. 1982, Bilej et al. 1989, 1989.

At the end of incubation, the cell suspension was rubbed on microscope lamellae and the smears were evaluated under optical microscope after Giemsa staining.

Cells containing at least three particles were considered positive.

The mean results are shown graphically in Figure 1. They clearly show that both A0 and A2 strongly stimulate phagocytosis in monocytes and granulocytes.

EXAMPLE 9: Effect of oligosaccharides on phagocytosis of cells from the peritoneal cavity:

A group of Balb/c mice (Jackson laboratory, Bar Harbor, ME, USA) were injected intraperi-torneally with either a control, LAM7, LAM5, A0 or A2.

After 24 hours, the mice were sacrificed, the peritoneal cells were collected in a Hanks (Sigma) medium.

After cell counts in a haemocytometer, the peritoneal cells were diluted tolx107 in a 1640 RPMI medium (Sigma) with 5% foetal calf serum (Hyclone, Logan, UT, USA). 2x106 cells in 0.2 mil of medium RPMI 1640 with 5% foetal calf serum were mixed with the same volume of HEMA particles (5x108/ml).

The suspension was incubated for 60 minutes at 37°C with occasional moderate agitation, the incubation was completed by centrifugation (150 g for 5 minutes) and the ball was resuspended.

Macrophages with ingested particles were counted under an optical microscope in Accustain-colored smears (modified Wright dye, Sigma).

Cells containing at least six particles were considered positive.

The mean results are shown graphically in Figure 2.They show that both A0 and A2 strongly stimulate phagocytosis in both monocytes and granulocytes of peritoneal macrophages.

EXAMPLE 10: Effect of A0 and A2 on a differential blood count

Using the same experimental groups as in example 8, two additional microscopic lamellae were prepared from each experimental sample. After Giemsa staining, the presence of individual cell types, i.e. monocytes, lymphocytes and granulocytes, was assessed for each lamellae under the optical microscope.

The mean results are shown graphically in Figure 3. They show that both A0 and A2 increase the number of monocytes and granulocytes in the peripheral blood.

EXAMPLE 11: Effect of A0 and A2 on a differential count in peritoneal cells

Using the same experimental groups as in example 8, two additional microscopic lamellae were prepared from each experimental sample. After Giemsa staining, the presence of individual cell types, i.e. macrophages, lymphocytes and mast cells, was assessed for each lamellae under the optical microscope.

The mean results are shown graphically in Figure 4. They show that both A0 and A2 increase the number of monocytes and granulocytes in the peritoneal cavity.

	Lev	NAP	4,51/8,1	5,1219,1	3,76/9,1	3,83/9,1	3,44/5,1	4,39/10,4	3,85/10,4
	Lev	H	4,56/8,0	4,99/9,1	3,61/9,1	3,86/9,1	3,42/5,1	4,36/10,4	3,80/10,4
	H	NAP	4,50/7,6	3,70/8,9	3,72/8,9	3,76/9,9	3,45/5,1	4,38/10,2	3,84/10,2

	Lev	NAP	100,1	73,2	78,1	81,5	66,2	68,6
	Lev	H	99,8	74,5	72,0	80,5	66,2	68,5
	H	NAP	102,2	74,5	80,0	81,3	66,5	68,7

	Lev	NAP	4,9317,1	5,26/7,1	3,85/9,1	3,95/9,1	3,43/4.9	4,13/10,4	3,68/10,4	4,45/7,8	5.06/8,9	3,97/8,9	3,80/8.9	3,43/4,9	4,35/10,4	3,81/10,4
	Lev	H	5,0216,8	5,1417,1	3,99/9,3	3.75/9.3	3.46/5.1	4,18/10,6	3,70/10,6	4,49/7,5	5,09/8,4	4,04/9,1	3.78/9.1	3,49/4,8	4,39/10,6	3,82/10,6
	H	NAP	4,95/7,1	5,36/7,5	3,96/9,1	3,75/9,1	3,38/4,9	4,19/10,4	3,62/10.4	4,37/7,8	3,50/8,6	3,88/9.0	3.77/9.0	3,45/5,1	4,32/10,6	3,78/10,6

	Lev	NAP	100,1	74,0	78,1	80,7	65,9	88,8	99,8	72,9	77,5	79,7	66,3	68,6
	Lev	H	100,0	75,6	72,5	80,5	65,8	68,6	99,7	72,9	77,6	79,6	66,2	68,6
	H	NAP	101,1	74,0	77,8	81,3	66,0	68,6	102,1	74,1	79,2	81,1	66,5	68,7

Claims (9)

1. A compound of general formula (I') or of general formula (II'): wherein R₁ represents H or OH and n is an integer from 2 to 10, preferably from 2 to 7, and more preferably equal to 3, 4 or 5.
2. The compound according to claim 1, wherein said compound is selected from β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-(α,β)-D-mannopyranose; β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-β-D-mannopyranose; β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-4-deoxy-(α,β)-D-deoxy-mannopyranose; β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-mannitol; β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-4-deoxy-mannitol; β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-mannitol; β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-4-deoxy-(α,β)-D-mannopyranose; and β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-4-deoxy-mannitol.
3. A method for preparing a compound according to claim 1 or 2 comprising a reaction between a glycosyl donor of formula (D) below and a glycosyl acceptor of formula (A) below: wherein

   m is an integer from 1 to 9, preferably from 1 to 6, and more preferably equal to 2, 3 or 4;

   p is an integer from 0 to 9, preferably from 0 to 6, and more preferably equal to 2, 3 or 4;

   R represents alkyl such as ethyl, methyl, propyl or butyl, or aryl such as phenyl or tolyl; R₂ represents allyl, methylnaphthyl, benzyl, paramethoxybenzyl, halogenoacetyl (chloroacetyl, bromoacetyl, iodoacetyl);

   R₃ and R₄, on the one hand, and R₃' and R₄', on the other hand, together form an ethylidyl, isopropylidyl, hexafluoroisopropylidyl, cyclopentylidyl, cyclohexylidyl, cycloheptylidyl, butylidyl, 1-tertiobutylethylidyl, benzylidyl, methoxybenzylidyl, 1-phenylbenzylidyl radical or R₃, R₄, R₃' and R₄' represent each independently of each other a benzyl, chlorobenzyl, nitrobenzyl, allyl, triarylmethyl, trialkylsilyl such as triethylsilyl, tri-isopropylsilyl, tertiobutyldimethylsilyl, ester such as acetyl, chloroacetyl, benzoyl, pivaloyl;

   R₅ represents H, a levulinoyl, acetyl, chloroacetyl, fluorenylmethyloxycarbonyl, trialkylsilyl group such as triethylsilyl, tri-isopropylsilyl, tertiobutyldimethylsilyl, preferably a levulinoyl group,

   provided that none of R₃, R₄, R₃', R₄' is identical to R₅.
4. The method according to claim 3, wherein the compound of formula (A) is
5. The method according to claim 3, wherein the compound of formula (D) is
6. A method for preparing a compound according to claim 1 or claim 2, comprising a step of epimerization in position 2 of the terminal entity.
7. A compound selected from the compounds of formulae (III), (IV), (V) and (VI) wherein

   p is an integer from 0 to 9, preferably from 0 to 6, and more preferably equal to 2, 3 or 4;

   R₂ represents hydrogen, allyl, methylnaphthyl, benzyl, paramethoxybenzyl, halogenoacetyl (chloroacetyl, bromoacetyl, iodoacetyl);

   R₃ and R₄, on the one hand, and R'₃ and R'₄, on the other hand, together form an ethylidyl, isopropylidyl, hexafluoroisopropylidyl, cyclopentylidyl, cyclohexylidyl, cycloheptylidyl, butylidyl, 1-tertiobutylethylidyl, benzylidyl, methoxybenzylidyl, 1-phenylbenzylidyl radical,

   or R₃, R₄ R₃' and R₄' represent each independently of each other a benzyl, chlorobenzyl, nitrobenzyl, allyl, triarylmethyl, trialkylsilyl such as triethylsilyl, tri-isopropylsilyl, tertiobutyldimethylsilyl, ester such as acetyl, chloroacetyl, benzoyl, pivaloyl;

   R₅ represents H, a levulinoyl, acetyl, chloroacetyl, fluorenylmethyloxycarbonyl, trialkylsilyl group such as triethylsilyl, tri-isopropylsilyl, tertiobutyldimethylsilyl, preferably a levulinoyl group,

   provided that none of R₃, R₄, R₃', R₄' is identical to R₅;

   R₇ represents an ester, in particular acetyl, benzoyl, pivaloyl, preferably Bz;

   R₈, a group orthogonal to all the other protective groups, which can be chosen from Bn, NAP, p-methoxybenzyl, p-methoxyphenyl, allyl, and preferably R₈ represents Bn,

   R₉ represents OR₈ or X.
8. A medicine comprising a compound as defined in claim 1 or 2.
9. The compound as defined in claim 1 or 2 for use in a method for treatment of a disease selected from the group consisting of tumour, cancer, viral disease, bacterial disease, fungal disease, disease of the immune system, auto-immune disease or disease linked to a deficiency in immunostimulation, in warm-blooded animals and human beings.