JPH0579656B2 - - Google Patents
Info
- Publication number
- JPH0579656B2 JPH0579656B2 JP58109979A JP10997983A JPH0579656B2 JP H0579656 B2 JPH0579656 B2 JP H0579656B2 JP 58109979 A JP58109979 A JP 58109979A JP 10997983 A JP10997983 A JP 10997983A JP H0579656 B2 JPH0579656 B2 JP H0579656B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- general formula
- optically active
- acid ester
- represented
- 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 - Lifetime
Links
- 108090000371 Esterases Proteins 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 23
- 244000005700 microbiome Species 0.000 claims description 13
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 2
- 239000000243 solution Substances 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 150000001733 carboxylic acid esters Chemical class 0.000 description 20
- 238000000034 method Methods 0.000 description 20
- 108090001060 Lipase Proteins 0.000 description 18
- 239000004367 Lipase Substances 0.000 description 18
- 102000004882 Lipase Human genes 0.000 description 18
- 235000019421 lipase Nutrition 0.000 description 18
- -1 carboxylic acid ester compounds Chemical class 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000006460 hydrolysis reaction Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 230000003287 optical effect Effects 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000007062 hydrolysis Effects 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000000926 separation method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 241000186063 Arthrobacter Species 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000235527 Rhizopus Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 241000228212 Aspergillus Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 3
- 241000588881 Chromobacterium Species 0.000 description 3
- 241000235395 Mucor Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000589516 Pseudomonas Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VNJOYCDHXKDFAJ-UHFFFAOYSA-N (2-methyl-4-oxo-3-prop-2-ynylcyclopent-2-en-1-yl) acetate Chemical compound CC(=O)OC1CC(=O)C(CC#C)=C1C VNJOYCDHXKDFAJ-UHFFFAOYSA-N 0.000 description 2
- KZYVOZABVXLALY-MRVPVSSYSA-N (4r)-4-hydroxy-3-methyl-2-prop-2-enylcyclopent-2-en-1-one Chemical compound CC1=C(CC=C)C(=O)C[C@H]1O KZYVOZABVXLALY-MRVPVSSYSA-N 0.000 description 2
- ISFGTDAAYLSOFY-MRVPVSSYSA-N (4r)-4-hydroxy-3-methyl-2-prop-2-ynylcyclopent-2-en-1-one Chemical compound CC1=C(CC#C)C(=O)C[C@H]1O ISFGTDAAYLSOFY-MRVPVSSYSA-N 0.000 description 2
- ASNHGEVAWNWCRQ-UHFFFAOYSA-N 4-(hydroxymethyl)oxolane-2,3,4-triol Chemical compound OCC1(O)COC(O)C1O ASNHGEVAWNWCRQ-UHFFFAOYSA-N 0.000 description 2
- 241000588986 Alcaligenes Species 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000588914 Enterobacter Species 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 241000186359 Mycobacterium Species 0.000 description 2
- 241000187654 Nocardia Species 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- 241000223252 Rhodotorula Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000187747 Streptomyces Species 0.000 description 2
- 241000223259 Trichoderma Species 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- KZYVOZABVXLALY-QMMMGPOBSA-N (4s)-4-hydroxy-3-methyl-2-prop-2-enylcyclopent-2-en-1-one Chemical compound CC1=C(CC=C)C(=O)C[C@@H]1O KZYVOZABVXLALY-QMMMGPOBSA-N 0.000 description 1
- ISFGTDAAYLSOFY-QMMMGPOBSA-N (4s)-4-hydroxy-3-methyl-2-prop-2-ynylcyclopent-2-en-1-one Chemical compound CC1=C(CC#C)C(=O)C[C@@H]1O ISFGTDAAYLSOFY-QMMMGPOBSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KZYVOZABVXLALY-UHFFFAOYSA-N 4-hydroxy-3-methyl-2-prop-2-enylcyclopent-2-en-1-one Chemical compound CC1=C(CC=C)C(=O)CC1O KZYVOZABVXLALY-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 241000590020 Achromobacter Species 0.000 description 1
- 241000908198 Actinomucor Species 0.000 description 1
- 241000223651 Aureobasidium Species 0.000 description 1
- 241000186216 Corynebacterium Species 0.000 description 1
- 241001337994 Cryptococcus <scale insect> Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000589565 Flavobacterium Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 241000186660 Lactobacillus Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000192041 Micrococcus Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000235648 Pichia Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- MDRWCGJDFKIFNQ-SNVBAGLBSA-N [(1r)-2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl] methanesulfonate Chemical compound CC1=C(CC=C)C(=O)C[C@H]1OS(C)(=O)=O MDRWCGJDFKIFNQ-SNVBAGLBSA-N 0.000 description 1
- HEMGRECXQITKQP-SNVBAGLBSA-N [(1r)-2-methyl-4-oxo-3-prop-2-ynylcyclopent-2-en-1-yl] methanesulfonate Chemical compound CC1=C(CC#C)C(=O)C[C@H]1OS(C)(=O)=O HEMGRECXQITKQP-SNVBAGLBSA-N 0.000 description 1
- MDFPPPIHFJPKRF-NSHDSACASA-N [(1s)-2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl] acetate Chemical compound CC(=O)O[C@H]1CC(=O)C(CC=C)=C1C MDFPPPIHFJPKRF-NSHDSACASA-N 0.000 description 1
- VNJOYCDHXKDFAJ-NSHDSACASA-N [(1s)-2-methyl-4-oxo-3-prop-2-ynylcyclopent-2-en-1-yl] acetate Chemical compound CC(=O)O[C@H]1CC(=O)C(CC#C)=C1C VNJOYCDHXKDFAJ-NSHDSACASA-N 0.000 description 1
- UCTLHLZWKJIXJI-LXIBVNSESA-N [(3s,8r,9s,10r,13s,14s)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(Cl)=C(C=O)C[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 UCTLHLZWKJIXJI-LXIBVNSESA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- MBVZEDIBUZMQOR-UHFFFAOYSA-N cyclopenten-1-yl acetate Chemical class CC(=O)OC1=CCCC1 MBVZEDIBUZMQOR-UHFFFAOYSA-N 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229940039696 lactobacillus Drugs 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10997983A JPS601151A (ja) | 1983-06-17 | 1983-06-17 | 光学活性シクロペンテノロン類の製造法 |
| EP84303327A EP0127386B1 (en) | 1983-05-25 | 1984-05-16 | Process for producing optically active cyclopentenolones |
| DE8484303327T DE3465185D1 (en) | 1983-05-25 | 1984-05-16 | Process for producing optically active cyclopentenolones |
| US06/612,122 US4571436A (en) | 1983-05-25 | 1984-05-21 | Process for producing optically active cyclopentenolones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10997983A JPS601151A (ja) | 1983-06-17 | 1983-06-17 | 光学活性シクロペンテノロン類の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS601151A JPS601151A (ja) | 1985-01-07 |
| JPH0579656B2 true JPH0579656B2 (US07709020-20100504-C00041.png) | 1993-11-04 |
Family
ID=14523998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10997983A Granted JPS601151A (ja) | 1983-05-25 | 1983-06-17 | 光学活性シクロペンテノロン類の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS601151A (US07709020-20100504-C00041.png) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0247620B1 (en) * | 1986-05-29 | 1993-05-05 | Sumitomo Chemical Company, Limited | Production of cyclopentenones |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52156840A (en) * | 1976-06-23 | 1977-12-27 | Roussel Uclaf | Sulfonic acid esters of optically active allethrolone* process for manufacture thereof and use thereof to inversion of allethrolone at asymmetric center |
| JPS5831994A (ja) * | 1981-08-20 | 1983-02-24 | Sumitomo Chem Co Ltd | （±）−アレスロロンの生化学的光学分割法 |
| JPS59186953A (ja) * | 1983-04-07 | 1984-10-23 | Sumitomo Chem Co Ltd | 光学活性シクロペンテノロンの製造法 |
-
1983
- 1983-06-17 JP JP10997983A patent/JPS601151A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52156840A (en) * | 1976-06-23 | 1977-12-27 | Roussel Uclaf | Sulfonic acid esters of optically active allethrolone* process for manufacture thereof and use thereof to inversion of allethrolone at asymmetric center |
| JPS5831994A (ja) * | 1981-08-20 | 1983-02-24 | Sumitomo Chem Co Ltd | （±）−アレスロロンの生化学的光学分割法 |
| JPS59186953A (ja) * | 1983-04-07 | 1984-10-23 | Sumitomo Chem Co Ltd | 光学活性シクロペンテノロンの製造法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS601151A (ja) | 1985-01-07 |
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