GB806935A - Process of reacting carbohydrates and polyhydric alcohols derived therefrom with various reagents - Google Patents
Process of reacting carbohydrates and polyhydric alcohols derived therefrom with various reagentsInfo
- Publication number
- GB806935A GB806935A GB2417556A GB2417556A GB806935A GB 806935 A GB806935 A GB 806935A GB 2417556 A GB2417556 A GB 2417556A GB 2417556 A GB2417556 A GB 2417556A GB 806935 A GB806935 A GB 806935A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrrolidone
- sucrose
- reacted
- methyl
- give
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 235000014633 carbohydrates Nutrition 0.000 title abstract 4
- 239000003153 chemical reaction reagent Substances 0.000 title abstract 4
- 150000001720 carbohydrates Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 150000005846 sugar alcohols Polymers 0.000 title abstract 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 15
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 abstract 9
- 229930006000 Sucrose Natural products 0.000 abstract 9
- 239000005720 sucrose Substances 0.000 abstract 9
- 238000006243 chemical reaction Methods 0.000 abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 229910052708 sodium Inorganic materials 0.000 abstract 3
- 239000011734 sodium Substances 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 2
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 abstract 2
- 238000006136 alcoholysis reaction Methods 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- 150000002605 large molecules Chemical class 0.000 abstract 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 2
- 235000021317 phosphate Nutrition 0.000 abstract 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 abstract 2
- -1 thio alcohols Chemical class 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- RCHDLEVSZBOHOS-UHFFFAOYSA-N 1,4-dichlorobut-2-yne Chemical compound ClCC#CCCl RCHDLEVSZBOHOS-UHFFFAOYSA-N 0.000 abstract 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 abstract 1
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 abstract 1
- YTBSYETUWUMLBZ-QWWZWVQMSA-N D-threose Chemical compound OC[C@@H](O)[C@H](O)C=O YTBSYETUWUMLBZ-QWWZWVQMSA-N 0.000 abstract 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 abstract 1
- 229920001202 Inulin Polymers 0.000 abstract 1
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 abstract 1
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- PAJZZWXQDKRLCV-UHFFFAOYSA-N [Zn].NCl Chemical compound [Zn].NCl PAJZZWXQDKRLCV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 abstract 1
- 235000012343 cottonseed oil Nutrition 0.000 abstract 1
- 239000002385 cottonseed oil Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 150000004676 glycans Polymers 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 abstract 1
- 229940029339 inulin Drugs 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 229920000768 polyamine Polymers 0.000 abstract 1
- 239000005017 polysaccharide Substances 0.000 abstract 1
- 150000004804 polysaccharides Polymers 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- FJOLTQXXWSRAIX-UHFFFAOYSA-K silver phosphate Chemical compound [Ag+].[Ag+].[Ag+].[O-]P([O-])([O-])=O FJOLTQXXWSRAIX-UHFFFAOYSA-K 0.000 abstract 1
- 229940019931 silver phosphate Drugs 0.000 abstract 1
- 229910000161 silver phosphate Inorganic materials 0.000 abstract 1
- 150000003445 sucroses Chemical class 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 150000004043 trisaccharides Chemical class 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Abstract
At least one hydroxy group of a carbohydrate or polyhydric alcohol derived therefrom is reacted with a reagent reactive with said hydroxy group in an inert solvent selected from 2-pyrrolidone and N-methyl-2-pyrrolidone (for numerous specified reagents see Group IV (b)). In examples: (2) octastearyl sucrose is used together with dioctyl phthalate to plasticise polyvinyl chloride; (5) sucrose is reacted with maleic anhydride in N-methyl-2-pyrrolidone to give a high molecular weight compound of probable formula <FORM:0806935/IV (a)/1> which may be further reacted through the double bond with polymerizable vinyl compounds such as styrene; (8) sucrose is reacted with 1,4-dichloro-2-butyne in 2-pyrrolidone to give a product of general formula <FORM:0806935/IV (a)/2> which may be further reacted with polyamines through the unsaturated bond; (14) inulin is reacted with maleic anhydride in N-methyl-2-pyrolidone to give a high molecular weight compound of probable formula <FORM:0806935/IV (a)/3>ALSO:At least one hydroxy group of a carbohydrate or polyhydric alcohol derived therefrom is reacted with a reagent reactive with said hydroxy group in an inert solvent selected from 2-pyrrolidone and N-methyl-2-pyrrolidone. The method may be used for esterifying the hydroxy compound with organic or inorganic acids (many specified), acid anhydrides or acid halides or by alcoholysis; nitrous anhydride gives nitrous esters; phosphorus oxychloride gives phosphates; zinc chloramine gives amines. The action of phosphorus tri- or penta-halides gives halo-derivatives from which may be obtained: nitriles by reaction with KCN; thio alcohols by reaction with KSH; phosphates by reaction with silver phosphate and amines by reaction with ammonia. Reaction with an alkali metal such as Na, K or Li gives carbohydralates or alcoholates which may be recovered by evaporation or precipitation with dioxan; these metal derivatives may be reacted with halides, including those prepared by the process of the invention, to give ethers. Numerous mono-, di-, tri- and poly-saccharides and carbohydrate alcohols are mentioned as suitable. In examples: (1) and (10) sodium sucrosate and sodium glucosate respectively are prepared by reacting the sugar with sodium metal dissolved in N-methyl-2-pyrrolidone; (2) and (6) octastearyl sucrose, (3) tetrastearyl sucrose, (11) octastearyl rhamnose, and (12) tetrastearyl threose are prepared by the action of stearyl chloride on the sugar in solution in one or other pyrrolidone; (4) sucrose and (13) raffinose are reacted with acetic anhydride in N-methyl-2-pyrrolidone to give, probably, sucrose and raffinose tetra-acetates; (7) a partially chlorinated sucrose is prepared by the action of sulphuryl chloride on sucrose in N-methyl-2-pyrrolidone; (9) alcoholysis is effected between sucrose and cottonseed oil in the presence of sodium methylate in N-methyl-2-pyrrolidone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2417556A GB806935A (en) | 1956-08-07 | 1956-08-07 | Process of reacting carbohydrates and polyhydric alcohols derived therefrom with various reagents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2417556A GB806935A (en) | 1956-08-07 | 1956-08-07 | Process of reacting carbohydrates and polyhydric alcohols derived therefrom with various reagents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB806935A true GB806935A (en) | 1959-01-07 |
Family
ID=10207592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2417556A Expired GB806935A (en) | 1956-08-07 | 1956-08-07 | Process of reacting carbohydrates and polyhydric alcohols derived therefrom with various reagents |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB806935A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3087970A (en) * | 1959-10-19 | 1963-04-30 | Allied Chem | Synthesis of propargyl alcohol from formaldehyde and acetylene |
| US3495998A (en) * | 1967-12-27 | 1970-02-17 | Velsicol Chemical Corp | Resinous compositions |
| WO2008141765A1 (en) | 2007-05-18 | 2008-11-27 | Raffinerie Notre Dame - Orafti S.A. | Method for providing fragrance to a substrate; fragrance-containing substrate |
| US7989546B2 (en) | 2007-03-07 | 2011-08-02 | Beneo-Orafti S.A. | Natural rubber latex preservation |
| WO2015143169A1 (en) * | 2014-03-20 | 2015-09-24 | The University Of Akron | Novel materials derived from fermentation-produced rhamnolipids |
-
1956
- 1956-08-07 GB GB2417556A patent/GB806935A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3087970A (en) * | 1959-10-19 | 1963-04-30 | Allied Chem | Synthesis of propargyl alcohol from formaldehyde and acetylene |
| US3495998A (en) * | 1967-12-27 | 1970-02-17 | Velsicol Chemical Corp | Resinous compositions |
| US7989546B2 (en) | 2007-03-07 | 2011-08-02 | Beneo-Orafti S.A. | Natural rubber latex preservation |
| WO2008141765A1 (en) | 2007-05-18 | 2008-11-27 | Raffinerie Notre Dame - Orafti S.A. | Method for providing fragrance to a substrate; fragrance-containing substrate |
| US8496994B2 (en) | 2007-05-18 | 2013-07-30 | Raffinerie Notre Dame-Orafti S.A. | Method for providing fragrance to a substrate; fragrance-containing substrate |
| WO2015143169A1 (en) * | 2014-03-20 | 2015-09-24 | The University Of Akron | Novel materials derived from fermentation-produced rhamnolipids |
| US10344304B2 (en) | 2014-03-20 | 2019-07-09 | The University Of Akron | Materials derived from fermentation-produced rhamnolipids and methods of production |
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