FR2457864A2 - Chiral synthesis for prepn. of cerulenin enantiomers - starting from 5,6-di:desoxy 1,2-O-isopropylidene-alpha-d-xylo-hex-5-eno:furanose - Google Patents
Chiral synthesis for prepn. of cerulenin enantiomers - starting from 5,6-di:desoxy 1,2-O-isopropylidene-alpha-d-xylo-hex-5-eno:furanoseInfo
- Publication number
- FR2457864A2 FR2457864A2 FR7914214A FR7914214A FR2457864A2 FR 2457864 A2 FR2457864 A2 FR 2457864A2 FR 7914214 A FR7914214 A FR 7914214A FR 7914214 A FR7914214 A FR 7914214A FR 2457864 A2 FR2457864 A2 FR 2457864A2
- Authority
- FR
- France
- Prior art keywords
- cerulenin
- chiral synthesis
- desoxy
- furanose
- prepn
- 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.)
- Pending
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 3
- 238000003786 synthesis reaction Methods 0.000 title abstract 3
- GVEZIHKRYBHEFX-NQQPLRFYSA-N cerulenin Chemical class C\C=C\C\C=C\CCC(=O)[C@H]1O[C@H]1C(N)=O GVEZIHKRYBHEFX-NQQPLRFYSA-N 0.000 title abstract 2
- LLHRMWHYJGLIEV-UHFFFAOYSA-N desoxy Chemical group COC1=CC(CCN)=CC(OC)=C1C LLHRMWHYJGLIEV-UHFFFAOYSA-N 0.000 title 1
- 150000002243 furanoses Chemical class 0.000 title 1
- -1 RADICAL HYDROCARBON Chemical class 0.000 abstract 2
- GVEZIHKRYBHEFX-MNOVXSKESA-N 13C-Cerulenin Natural products CC=CCC=CCCC(=O)[C@H]1O[C@@H]1C(N)=O GVEZIHKRYBHEFX-MNOVXSKESA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- GVEZIHKRYBHEFX-UHFFFAOYSA-N caerulein A Natural products CC=CCC=CCCC(=O)C1OC1C(N)=O GVEZIHKRYBHEFX-UHFFFAOYSA-N 0.000 abstract 1
- 229950005984 cerulenin Drugs 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
- C07H9/04—Cyclic acetals
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
PROCEDE DE SYNTHESE CHIRALE DES ENONTIOMERES DE FORMULE: (CF DESSIN DANS BOPI) (R RADICAL HYDROCARBONE, SATURE OU NON, EN C1-C12). CE PROCEDE COMPREND LES ETAPES:(A) (CF DESSIN DANS BOPI) R GROUPE PARTANT R GROUPE ACETALIQUE OU BENZYLE A LA SYNTHESE CHIRALE DE LA CERULENINE ET DE SES DERIVES.CHIRAL SYNTHESIS OF THE ENONTIOMERS OF FORMULA: (CF DRAWING IN BOPI) (R RADICAL HYDROCARBON, SATURATED OR NOT, IN C1-C12). THIS PROCESS INCLUDES THE STEPS: (A) (CF DRAWING IN BOPI) R START GROUP R ACETALIC OR BENZYL GROUP TO CHIRAL SYNTHESIS OF CERULENIN AND ITS DERIVATIVES.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7914214A FR2457864A2 (en) | 1979-06-01 | 1979-06-01 | Chiral synthesis for prepn. of cerulenin enantiomers - starting from 5,6-di:desoxy 1,2-O-isopropylidene-alpha-d-xylo-hex-5-eno:furanose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7914214A FR2457864A2 (en) | 1979-06-01 | 1979-06-01 | Chiral synthesis for prepn. of cerulenin enantiomers - starting from 5,6-di:desoxy 1,2-O-isopropylidene-alpha-d-xylo-hex-5-eno:furanose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2457864A2 true FR2457864A2 (en) | 1980-12-26 |
Family
ID=9226181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7914214A Pending FR2457864A2 (en) | 1979-06-01 | 1979-06-01 | Chiral synthesis for prepn. of cerulenin enantiomers - starting from 5,6-di:desoxy 1,2-O-isopropylidene-alpha-d-xylo-hex-5-eno:furanose |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2457864A2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2531961A1 (en) * | 1982-08-18 | 1984-02-24 | Chevron Res | 5-DEOXY-3-O- (ARYLMETHYL OR SUBSTITUTED ARYLMETHYL) -1,2-O-ALKYLIDENE-A-D-XYLOFURANOSES, HERBICIDAL COMPOSITIONS CONTAINING SAME AND APPLICATIONS THEREOF |
| US8158677B2 (en) | 2007-06-01 | 2012-04-17 | The Trustees Of Princeton University | Treatment of viral infections by modulation of host cell metabolic pathways |
-
1979
- 1979-06-01 FR FR7914214A patent/FR2457864A2/en active Pending
Non-Patent Citations (3)
| Title |
|---|
| EXBK/75 * |
| EXBK/77 * |
| EXBK/78 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2531961A1 (en) * | 1982-08-18 | 1984-02-24 | Chevron Res | 5-DEOXY-3-O- (ARYLMETHYL OR SUBSTITUTED ARYLMETHYL) -1,2-O-ALKYLIDENE-A-D-XYLOFURANOSES, HERBICIDAL COMPOSITIONS CONTAINING SAME AND APPLICATIONS THEREOF |
| US8158677B2 (en) | 2007-06-01 | 2012-04-17 | The Trustees Of Princeton University | Treatment of viral infections by modulation of host cell metabolic pathways |
| EP2572712A2 (en) | 2007-06-01 | 2013-03-27 | The Trustees Of Princeton University | Treatment of viral infections by modulation of host cell metabolic pathways |
| EP2581081A2 (en) | 2007-06-01 | 2013-04-17 | The Trustees Of Princeton University | Treatment of viral infections by modulation of host cell metabolic pathways |
| US9029413B2 (en) | 2007-06-01 | 2015-05-12 | The Trustees Of Princeton University | Treatment of viral infections by modulation of host cell metabolic pathways |
| US9757407B2 (en) | 2007-06-01 | 2017-09-12 | The Trustees Of Princeton University | Treatment of viral infections by modulation of host cell metabolic pathways |
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