JPS59156290A - 光学活性アルキルまたはアルケニルアリ−ルスルホキシドの製造法 - Google Patents
光学活性アルキルまたはアルケニルアリ−ルスルホキシドの製造法Info
- Publication number
- JPS59156290A JPS59156290A JP3208183A JP3208183A JPS59156290A JP S59156290 A JPS59156290 A JP S59156290A JP 3208183 A JP3208183 A JP 3208183A JP 3208183 A JP3208183 A JP 3208183A JP S59156290 A JPS59156290 A JP S59156290A
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- sulfide
- sulfoxide
- alkenylaryl
- alkyl
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 13
- -1 alkenylaryl sulfoxide Chemical class 0.000 title claims abstract description 10
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 241000186216 Corynebacterium Species 0.000 claims abstract description 7
- 150000003462 sulfoxides Chemical class 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 abstract description 10
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 239000000758 substrate Substances 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 241000894006 Bacteria Species 0.000 abstract description 5
- 230000003287 optical effect Effects 0.000 abstract description 5
- 150000003333 secondary alcohols Chemical class 0.000 abstract description 2
- 150000003431 steroids Chemical class 0.000 abstract description 2
- 150000001261 hydroxy acids Chemical class 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 description 12
- 239000002609 medium Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000158504 Rhodococcus hoagii Species 0.000 description 6
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229910017053 inorganic salt Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- PKAZBZIEOSJIDC-UHFFFAOYSA-N decylsulfanylbenzene Chemical compound CCCCCCCCCCSC1=CC=CC=C1 PKAZBZIEOSJIDC-UHFFFAOYSA-N 0.000 description 2
- YXTMHCMKLBGJAC-UHFFFAOYSA-N decylsulfinylbenzene Chemical compound CCCCCCCCCCS(=O)C1=CC=CC=C1 YXTMHCMKLBGJAC-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- QGNRLAFFKKBSIM-UHFFFAOYSA-N prop-2-enylsulfanylbenzene Chemical compound C=CCSC1=CC=CC=C1 QGNRLAFFKKBSIM-UHFFFAOYSA-N 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- IXULCOYQSDIBFO-UHFFFAOYSA-N (3-bromothiophen-2-yl)methanol Chemical compound OCC=1SC=CC=1Br IXULCOYQSDIBFO-UHFFFAOYSA-N 0.000 description 1
- JXTGICXCHWMCPM-UHFFFAOYSA-N (methylsulfinyl)benzene Chemical compound CS(=O)C1=CC=CC=C1 JXTGICXCHWMCPM-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001467496 Coriobacterium Species 0.000 description 1
- 102100036883 Cyclin-H Human genes 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 102100028138 F-box/WD repeat-containing protein 7 Human genes 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 101000713120 Homo sapiens Cyclin-H Proteins 0.000 description 1
- 101001060231 Homo sapiens F-box/WD repeat-containing protein 7 Proteins 0.000 description 1
- 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 description 1
- 241001465754 Metazoa Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VHILIAIEEYLJNA-UHFFFAOYSA-N methyl p-tolyl sulfide Chemical compound CSC1=CC=C(C)C=C1 VHILIAIEEYLJNA-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 150000003453 sulfinic acid esters Chemical class 0.000 description 1
- IWOKCMBOJXYDEE-UHFFFAOYSA-N sulfinylmethane Chemical compound C=S=O IWOKCMBOJXYDEE-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3208183A JPS59156290A (ja) | 1983-02-28 | 1983-02-28 | 光学活性アルキルまたはアルケニルアリ−ルスルホキシドの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3208183A JPS59156290A (ja) | 1983-02-28 | 1983-02-28 | 光学活性アルキルまたはアルケニルアリ−ルスルホキシドの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59156290A true JPS59156290A (ja) | 1984-09-05 |
| JPH0365953B2 JPH0365953B2 (https=) | 1991-10-15 |
Family
ID=12348926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3208183A Granted JPS59156290A (ja) | 1983-02-28 | 1983-02-28 | 光学活性アルキルまたはアルケニルアリ−ルスルホキシドの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59156290A (https=) |
-
1983
- 1983-02-28 JP JP3208183A patent/JPS59156290A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0365953B2 (https=) | 1991-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1258818A (en) | Process for producing diol and furan and microorganism capable of same | |
| US4338251A (en) | Two-functional-group-containing terpenoids, processes for the preparation of the same, and anti-ulcer agents containing the same | |
| JPS59156290A (ja) | 光学活性アルキルまたはアルケニルアリ−ルスルホキシドの製造法 | |
| JPH0285289A (ja) | マクロライド化合物 | |
| JPH02218688A (ja) | マクロライド化合物 | |
| US4468458A (en) | Two-functional-group-containing terpenoids, processes for the preparation of the same, and anti-ulcer agents containing the same | |
| JP2746372B2 (ja) | Ｆ−０３６８物質 | |
| DK146190D0 (da) | Hidtil ukendte forbindelser | |
| KR820000295B1 (ko) | 코엔자임 q의 제조방법 | |
| US3835170A (en) | Hypotensive agent, oudenone, its salts and processes for production and preparation thereof | |
| US4468459A (en) | Process for the preparation of polyprenyl ketone derivatives | |
| KR940019724A (ko) | 약리학적 효과가 있는 아피오크레아 크리소스퍼마로 부터의 활성 펩타이드인 크리소스퍼민, 이의 제조방법 및 용도 | |
| JPS58126792A (ja) | 微生物による光学活性物質の製法 | |
| US5023348A (en) | Process for the preparation of macrolide compounds | |
| JPH01156992A (ja) | マクロライド化合物の製法 | |
| US3352759A (en) | Process for producing cis-succinic acid of gauche form | |
| CA1302407C (en) | Process for the preparation of macrolide compounds | |
| JPH054069B2 (https=) | ||
| US3849419A (en) | Antiviral antibiotic | |
| US3592735A (en) | 5-(hydroxyanilino)-1,2,3,4-thiatriazoles and method of making same | |
| US3407118A (en) | Process for microbiological side chain degradation of steroids of the pregnane series | |
| JPS62208298A (ja) | 光学活性α−ヒドロキシケトンおよびそのカルボン酸エステルの製造法 | |
| US3267004A (en) | Fermentation method for producing gentisic acid | |
| JP3262177B2 (ja) | 抗生物質ｎｋ１０９５８ｐその製造法及びそれを有効成分として含有する農園芸用除草剤、植物生長調節剤および殺菌剤 | |
| JPH03103185A (ja) | イソオレフィン化合物の製造方法 |