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 (enrdf_load_stackoverflow) | 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 (enrdf_load_stackoverflow) |
-
1983
- 1983-02-28 JP JP3208183A patent/JPS59156290A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0365953B2 (enrdf_load_stackoverflow) | 1991-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4386227A (en) | Two-functional-group-containing terpenoids | |
| CA1258818A (en) | Process for producing diol and furan and microorganism capable of same | |
| JPS5910798B2 (ja) | 新しいリフアマイシン類の製造方法 | |
| GB760112A (en) | Improvements in or relating to cultivation of plant tissue | |
| 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 | |
| KR820000295B1 (ko) | 코엔자임 q의 제조방법 | |
| CA1245589A (en) | Indanyl derivatives and process for their preparation | |
| US4468459A (en) | Process for the preparation of polyprenyl ketone derivatives | |
| JPH02257887A (ja) | ストレプトミセス属菌からの新規アングサイクリノンおよびその製造方法 | |
| 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 | |
| JP3217301B2 (ja) | 光学活性グリシド酸エステル及び光学活性グリセリン酸エステルの製造方法 | |
| CA1302407C (en) | Process for the preparation of macrolide compounds | |
| 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 | |
| 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 | |
| Fuganti et al. | On the synthesis of serine and homoserine samples asymmetrically labelled with tritium and deuterium in the hydroxymethylene group | |
| JPS60207592A (ja) | 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 | |
| JPS59102396A (ja) | 生理活性物質ｍｌ−２３６ｂの製造法 |