CS815087A2 - Method of optically active(-)-oxabicyclo/3,3,0/octanoles production - Google Patents
Method of optically active(-)-oxabicyclo/3,3,0/octanoles productionInfo
- Publication number
- CS815087A2 CS815087A2 CS878150A CS815087A CS815087A2 CS 815087 A2 CS815087 A2 CS 815087A2 CS 878150 A CS878150 A CS 878150A CS 815087 A CS815087 A CS 815087A CS 815087 A2 CS815087 A2 CS 815087A2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- oxabicyclo
- octanoles
- production
- optically active
- saponified
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000000707 stereoselective effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Process for the manufacture of (-)-oxabicyclo[3.3.0]octanolones of formula (-)-I, where R is hydrogen or the residue (a), in which R1 has the notation of a hydrogen, alkyl with 1-7 C atoms, or phenyl. The process is characterized in that a racemic oxabicyclo[3.3.0]-octanolone-acylate of formula (+/-)-II, where R1 has the above notation, is subjected to a stereo-specific acylate hydrolysis and the (-)-I (R = (a)) is separated from the saponified (+)-I (R = H) or the saponified (-)-I (R = H) is separated from the unsaponified (+)-II.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863638762 DE3638762A1 (en) | 1986-11-13 | 1986-11-13 | RACEMAT CLEAVAGE OF 7 (ALPHA) -ACYLOXY-6SS-HYDROXY-METHYL-2-OXABICYCLO (3.3.0) OCTAN-3-ONES BY STEREO-SPECIFIC ENZYMATIC ACYLATE HYDROLYSIS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS815087A2 true CS815087A2 (en) | 1989-08-14 |
| CS268841B2 CS268841B2 (en) | 1990-04-11 |
Family
ID=6313862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS878150A CS268841B2 (en) | 1986-11-13 | 1987-11-13 | Method of optically active(-)-oxabicyclo/3,3,0/octanoles production |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0271433B1 (en) |
| JP (1) | JPH01501360A (en) |
| AT (1) | ATE85084T1 (en) |
| BG (1) | BG48098A3 (en) |
| CS (1) | CS268841B2 (en) |
| DD (1) | DD279689A5 (en) |
| DE (2) | DE3638762A1 (en) |
| ES (1) | ES2053577T3 (en) |
| GR (1) | GR3007127T3 (en) |
| HU (1) | HU202289B (en) |
| WO (1) | WO1988003570A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9108376D0 (en) * | 1991-04-19 | 1991-06-05 | Enzymatix Ltd | Cyclopentenes |
| US5840923A (en) * | 1992-04-21 | 1998-11-24 | Chiroscience Limited | Chiral cyclopentene derivatives and their preparation |
| DE69330787T2 (en) * | 1992-04-21 | 2002-06-13 | Chirotech Technology Ltd., Cambridge | CHIRAL CYCLOPENTE DERIVATIVES AND THEIR PRODUCTION |
| US5215918A (en) * | 1992-06-19 | 1993-06-01 | Bend Research, Inc. | Enantiomeric enrichment of (R,S)-3-quinuclidinol |
| DE4435242A1 (en) * | 1994-10-04 | 1996-04-11 | Hoechst Ag | Process for the enzymatic separation of enantiomers of rac-2-oxotricyclo 2,2,1,0 · 3 ·, · 5 · -heptan-7-carboxylic acid or the -carboxylic acid ester |
| DE60124616T2 (en) | 2000-05-08 | 2007-09-13 | Pfizer Products Inc., Groton | Enzymatic cleavage of selective modulators of the estrogen receptor |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE431750B (en) * | 1977-05-26 | 1984-02-27 | Chinoin Gyogyszer Es Vegyeszet | PROCEDURE FOR THE PREPARATION OF BICYCLIC LACTON DIODE DERIVATIVES |
| DE3021895A1 (en) * | 1980-06-06 | 1981-12-24 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | NEW METHOD FOR PRODUCING CARBACYCLIN INTERMEDIATE PRODUCTS |
| DE3465185D1 (en) * | 1983-05-25 | 1987-09-10 | Sumitomo Chemical Co | Process for producing optically active cyclopentenolones |
| JPS61280294A (en) * | 1985-06-04 | 1986-12-10 | Nisshin Flour Milling Co Ltd | Optically active carbacycline intermediate and production thereof |
-
1986
- 1986-11-13 DE DE19863638762 patent/DE3638762A1/en not_active Withdrawn
-
1987
- 1987-11-11 DD DD87308937A patent/DD279689A5/en not_active IP Right Cessation
- 1987-11-12 ES ES87730148T patent/ES2053577T3/en not_active Expired - Lifetime
- 1987-11-12 EP EP87730148A patent/EP0271433B1/en not_active Expired - Lifetime
- 1987-11-12 HU HU875796A patent/HU202289B/en not_active IP Right Cessation
- 1987-11-12 JP JP62506741A patent/JPH01501360A/en active Pending
- 1987-11-12 WO PCT/DE1987/000520 patent/WO1988003570A1/en unknown
- 1987-11-12 AT AT87730148T patent/ATE85084T1/en not_active IP Right Cessation
- 1987-11-12 DE DE8787730148T patent/DE3783885D1/en not_active Expired - Lifetime
- 1987-11-13 CS CS878150A patent/CS268841B2/en unknown
-
1988
- 1988-07-12 BG BG084850A patent/BG48098A3/en unknown
-
1993
- 1993-02-23 GR GR930400363T patent/GR3007127T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS268841B2 (en) | 1990-04-11 |
| BG48098A3 (en) | 1990-11-15 |
| JPH01501360A (en) | 1989-05-18 |
| DD279689A5 (en) | 1990-06-13 |
| HU202289B (en) | 1991-02-28 |
| WO1988003570A1 (en) | 1988-05-19 |
| HUT47155A (en) | 1989-01-30 |
| ES2053577T3 (en) | 1994-08-01 |
| EP0271433A1 (en) | 1988-06-15 |
| DE3638762A1 (en) | 1988-05-26 |
| GR3007127T3 (en) | 1993-07-30 |
| EP0271433B1 (en) | 1993-01-27 |
| ATE85084T1 (en) | 1993-02-15 |
| DE3783885D1 (en) | 1993-03-11 |
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