JPS61189258A - 光学活性グリセロ−ル誘導体及びその製造方法 - Google Patents
光学活性グリセロ−ル誘導体及びその製造方法Info
- Publication number
- JPS61189258A JPS61189258A JP2889485A JP2889485A JPS61189258A JP S61189258 A JPS61189258 A JP S61189258A JP 2889485 A JP2889485 A JP 2889485A JP 2889485 A JP2889485 A JP 2889485A JP S61189258 A JPS61189258 A JP S61189258A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- optically active
- formulas
- mathematical
- group
- 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
- 150000002314 glycerols Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 102000004190 Enzymes Human genes 0.000 claims abstract description 20
- 108090000790 Enzymes Proteins 0.000 claims abstract description 20
- 241000589516 Pseudomonas Species 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 9
- 241000235527 Rhizopus Species 0.000 claims description 8
- 244000005700 microbiome Species 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 108090000371 Esterases Proteins 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000000707 stereoselective effect Effects 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- PHIQHXFUZVPYII-ZCFIWIBFSA-O (R)-carnitinium Chemical compound C[N+](C)(C)C[C@H](O)CC(O)=O PHIQHXFUZVPYII-ZCFIWIBFSA-O 0.000 abstract description 2
- 239000002876 beta blocker Substances 0.000 abstract description 2
- 229940097320 beta blocking agent Drugs 0.000 abstract description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 2
- 229960004203 carnitine Drugs 0.000 abstract description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 102000004882 Lipase Human genes 0.000 description 5
- 108090001060 Lipase Proteins 0.000 description 5
- 239000004367 Lipase Substances 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 235000019421 lipase Nutrition 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000007070 tosylation reaction Methods 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 108010013563 Lipoprotein Lipase Proteins 0.000 description 2
- 102000043296 Lipoprotein lipases Human genes 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 240000005384 Rhizopus oryzae Species 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 235000021581 juice product Nutrition 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 108700018454 CDC15 Proteins 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 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
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 101150081467 cdc15 gene Proteins 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012044 organic layer 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
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2889485A JPS61189258A (ja) | 1985-02-15 | 1985-02-15 | 光学活性グリセロ−ル誘導体及びその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2889485A JPS61189258A (ja) | 1985-02-15 | 1985-02-15 | 光学活性グリセロ−ル誘導体及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61189258A true JPS61189258A (ja) | 1986-08-22 |
| JPH0513147B2 JPH0513147B2 (enrdf_load_stackoverflow) | 1993-02-19 |
Family
ID=12261101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2889485A Granted JPS61189258A (ja) | 1985-02-15 | 1985-02-15 | 光学活性グリセロ−ル誘導体及びその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61189258A (enrdf_load_stackoverflow) |
-
1985
- 1985-02-15 JP JP2889485A patent/JPS61189258A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0513147B2 (enrdf_load_stackoverflow) | 1993-02-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0117228B1 (en) | Analogs of mevalonolactone and derivatives thereof, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals | |
| SU1442071A3 (ru) | Способ получени производных 4-ацетокси-3-оксиэтилазетидин-2-она (его варианты) | |
| JPH07501932A (ja) | ピラノン | |
| JPS63284184A (ja) | 光学活性化合物およびその製造方法 | |
| JPS61227797A (ja) | 光学活性グリコ−ル類の製造方法 | |
| JPH0156760B2 (enrdf_load_stackoverflow) | ||
| JPS61189258A (ja) | 光学活性グリセロ−ル誘導体及びその製造方法 | |
| JP2880231B2 (ja) | 光学活性アミノプロパンジオール誘導体及びその対掌体エステルの製造方法 | |
| EP0189878A2 (en) | Process for preparing optically active glycerol derivates | |
| JPH0573396B2 (enrdf_load_stackoverflow) | ||
| KR920006869B1 (ko) | 광학 활성 화합물 및 이의 제조방법 | |
| JP3010382B2 (ja) | （ｒ）−２−プロポキシベンゼン誘導体の製造法 | |
| JPH1014590A (ja) | 光学活性２−置換−３−フェニルプロピオン酸及びそのエステルの製造方法 | |
| JP2838527B2 (ja) | 光学活性化合物の製造法 | |
| EP0472336A1 (en) | Process for preparing optically active 3-hydroxybutane derivatives | |
| JPH01281098A (ja) | 光学活性カルボン酸及び光学活性カルボン酸エステルの製造方法 | |
| JPS62158250A (ja) | 光学活性グリセロ−ル誘導体の分離方法 | |
| JP2974181B2 (ja) | シクロブタノールの新規な製造法 | |
| JPH0513636B2 (enrdf_load_stackoverflow) | ||
| JP2538231B2 (ja) | 光学活性４−ペンテン−２−オ−ル誘導体の製造方法 | |
| JPS61173787A (ja) | 光学活性グリセロ−ル誘導体の製造方法 | |
| JPH0829115B2 (ja) | 光学活性１−ハロゲノ−２−アルカノ−ル誘導体の製造方法 | |
| JPS61289899A (ja) | 光学活性２−ハロ−１−フエニルエタノ−ルおよびそのエステルの製造法 | |
| JPH08119958A (ja) | 光学活性クロマン化合物の製造方法 | |
| JPH0662892A (ja) | 光学分割によるインドリン−２−カルボン酸の製造方法 |