CA1340738C - Derives du glycidol optiquement actifs - Google Patents

Derives du glycidol optiquement actifs

Info

Publication number: CA1340738C
Authority: CA; Canada
Prior art keywords: compound; purified; formula; purity; recrystallized
Prior art date: 1986-06-25
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 - Fee Related

Application number

CA 540572

Other languages

English (en)

Inventor

Karl Barry Sharpless

Janice Klunder

Tetsuo H. Onami

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Massachusetts Institute of Technology

Original Assignee

Massachusetts Institute of Technology

Priority date (The priority date 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 date listed.)

1986-06-25

Filing date

1987-06-25

Publication date

1999-09-14

1986-10-01 Priority claimed from US07/913,936 external-priority patent/US4946974A/en

1987-06-25 Application filed by Massachusetts Institute of Technology filed Critical Massachusetts Institute of Technology

1999-09-14 Application granted granted Critical

1999-09-14 Publication of CA1340738C publication Critical patent/CA1340738C/fr

2016-09-14 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical class OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 title abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 48
230000003287 optical effect Effects 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 10
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 4
101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
RPKWNMFDAOACCX-UHFFFAOYSA-N 4-chloro-3-nitrobenzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 RPKWNMFDAOACCX-UHFFFAOYSA-N 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
JOYKCMAPFCSKNO-UHFFFAOYSA-N chloro benzenesulfonate Chemical compound ClOS(=O)(=O)C1=CC=CC=C1 JOYKCMAPFCSKNO-UHFFFAOYSA-N 0.000 claims 1
UJJUJHTVDYXQON-UHFFFAOYSA-N nitro benzenesulfonate Chemical compound [O-][N+](=O)OS(=O)(=O)C1=CC=CC=C1 UJJUJHTVDYXQON-UHFFFAOYSA-N 0.000 claims 1
-1 glycidyl m-nitrobenzenesulfonate Chemical compound 0.000 abstract description 5
238000003786 synthesis reaction Methods 0.000 abstract description 4
RLSNBCGWRKVRQC-UHFFFAOYSA-N oxiran-2-ylmethyl 4-chloro-3-nitrobenzenesulfonate Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(S(=O)(=O)OCC2OC2)=C1 RLSNBCGWRKVRQC-UHFFFAOYSA-N 0.000 abstract description 2
OQKMEZWVWHLHIP-UHFFFAOYSA-N oxiran-2-ylmethyl 4-chlorobenzenesulfonate Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)OCC1OC1 OQKMEZWVWHLHIP-UHFFFAOYSA-N 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
238000000034 method Methods 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 7
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
XEBCWEDRGPSHQH-YUMQZZPRSA-N dipropan-2-yl (2s,3s)-2,3-dihydroxybutanedioate Chemical compound CC(C)OC(=O)[C@@H](O)[C@H](O)C(=O)OC(C)C XEBCWEDRGPSHQH-YUMQZZPRSA-N 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000002808 molecular sieve Substances 0.000 description 3
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
QYYCPWLLBSSFBW-UHFFFAOYSA-N 2-(naphthalen-1-yloxymethyl)oxirane Chemical compound C=1C=CC2=CC=CC=C2C=1OCC1CO1 QYYCPWLLBSSFBW-UHFFFAOYSA-N 0.000 description 2
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
241000521257 Hydrops Species 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
239000012267 brine Substances 0.000 description 2
238000006735 epoxidation reaction Methods 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000005259 measurement Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
229960003712 propranolol Drugs 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000011550 stock solution Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
AQHHHDLHHXJYJD-AWEZNQCLSA-N (2s)-1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=CC=C2C(OC[C@@H](O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-AWEZNQCLSA-N 0.000 description 1
CJVYYDCBKKKIPD-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetramethylbenzene-1,2-diamine Chemical compound CN(C)C1=CC=CC=C1N(C)C CJVYYDCBKKKIPD-UHFFFAOYSA-N 0.000 description 1
BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 1
ONMOULMPIIOVTQ-UHFFFAOYSA-M 3-Nitrobenzene sulphonate Chemical compound [O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-M 0.000 description 1
MWWNNNAOGWPTQY-UHFFFAOYSA-N 3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1 MWWNNNAOGWPTQY-UHFFFAOYSA-N 0.000 description 1
RPKWNMFDAOACCX-UHFFFAOYSA-M 4-chloro-3-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC(S([O-])(=O)=O)=CC=C1Cl RPKWNMFDAOACCX-UHFFFAOYSA-M 0.000 description 1
SEWNAJIUKSTYOP-UHFFFAOYSA-N 4-chloro-3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(S(Cl)(=O)=O)=CC=C1Cl SEWNAJIUKSTYOP-UHFFFAOYSA-N 0.000 description 1
ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
102100022210 COX assembly mitochondrial protein 2 homolog Human genes 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000861718 Chloris <Aves> Species 0.000 description 1
244000248349 Citrus limon Species 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
229910004373 HOAc Inorganic materials 0.000 description 1
101000900446 Homo sapiens COX assembly mitochondrial protein 2 homolog Proteins 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 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
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000000674 adrenergic antagonist Substances 0.000 description 1
150000004808 allyl alcohols Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000013459 approach Methods 0.000 description 1
OBRNDARFFFHCGE-QDSVTUBZSA-N arformoterol fumarate Chemical compound OC(=O)\C=C\C(O)=O.C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C(NC=O)=C1.C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C(NC=O)=C1 OBRNDARFFFHCGE-QDSVTUBZSA-N 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000008827 biological function Effects 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004296 chiral HPLC Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
238000009795 derivation Methods 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
XEBCWEDRGPSHQH-UHFFFAOYSA-N diisopropyl tartrate Chemical compound CC(C)OC(=O)C(O)C(O)C(=O)OC(C)C XEBCWEDRGPSHQH-UHFFFAOYSA-N 0.000 description 1
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
230000006870 function Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
SGFJJNBUMXQSMU-PDBXOOCHSA-N oxiran-2-ylmethyl (9z,12z,15z)-octadeca-9,12,15-trienoate Chemical class CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OCC1CO1 SGFJJNBUMXQSMU-PDBXOOCHSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007670 refining Methods 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
239000003579 shift reagent Substances 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Epoxy Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA 540572 1986-06-25 1987-06-25 Derives du glycidol optiquement actifs Expired - Fee Related CA1340738C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US87817686A	1986-06-25	1986-06-25
US878,176		1986-06-25
US913,936		1986-10-01
US07/913,936 US4946974A (en)	1986-10-01	1986-10-01	Optically active derivatives of glycidol

Publications (1)

Publication Number	Publication Date
CA1340738C true CA1340738C (fr)	1999-09-14

Family

ID=27128478

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 540572 Expired - Fee Related CA1340738C (fr)	1986-06-25	1987-06-25	Derives du glycidol optiquement actifs

Country Status (2)

Country	Link
CA (1)	CA1340738C (fr)
WO (1)	WO1988000190A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE468211B (sv) *	1990-01-22	1992-11-23	Nobel Chemicals Ab	Flerstegsfoerfarande foer framstaellning av homokirala aminer
GB9001832D0 (en) *	1990-01-26	1990-03-28	Ici Plc	Optical resolution
US5194637A (en) *	1991-08-22	1993-03-16	Syracuse University	Method and apparatus for synthesis of highly isomerically pure stereoisomers of glycidol derivatives
AU2003268512A1 (en)	2002-09-09	2004-03-29	Janssen Pharmaceutica N.V.	Hydroxy alkyl substituted 1,3,8-triazaspiro[4.5]decan-4-one derivatives useful for the treatment of ORL-1 receptor mediated disorders
CN103202840B (zh)	2006-11-28	2015-02-11	詹森药业有限公司	3-(3-氨基-2-(r)-羟基-丙基)-1-(4-氟-苯基)-8-(8-甲基-萘-1-基甲基)-1,3,8-三氮杂-螺[4.5]癸烷-4-酮的盐
EP2150552B1 (fr)	2007-04-09	2013-01-02	Janssen Pharmaceutica NV	Dérivés de 1,3,8-trisubstitué-1,3,8-triaza-spiro[4.5]décan-4-one utilisés comme ligands du récepteur orl-i dans le traitement de l'anxiété et de la dépression

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2755290A (en) *	1953-10-26	1956-07-17	Shell Dev	Esters of sulfonic acids and certain epoxy-substituted alcohols and method for theirpreparation
SE354851B (fr) *	1970-02-18	1973-03-26	Haessle Ab
US4145442A (en) *	1972-04-04	1979-03-20	Aktiebolaget Hassle	Phenoxy-hydroxypropylamines, their preparation, and method and pharmaceutical preparations for treating cardiovascular diseases
US4210653A (en) *	1978-06-27	1980-07-01	Merck & Co., Inc.	Pyridyloxypropanolamines
US4471130A (en) *	1980-08-06	1984-09-11	The Board Of Trustees Of The Leland Stanford Junior University	Method for asymmetric epoxidation
JPS5821692A (ja) *	1981-07-29	1983-02-08	Microbial Chem Res Found	新規アミノ配糖体
JPS60208973A (ja) *	1984-03-31	1985-10-21	Kowa Co	循環系疾患治療剤

1987
- 1987-06-24 WO PCT/US1987/001523 patent/WO1988000190A1/fr not_active Ceased
- 1987-06-25 CA CA 540572 patent/CA1340738C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
WO1988000190A1 (fr)	1988-01-14

Legal Events

Date	Code	Title	Description
2008-09-15	MKLA	Lapsed

Publication	Publication Date	Title
Boyd et al.	2000	Synthesis and absolute stereochemistry assignment of enantiopure dihydrofuro-and dihydropyrano-quinoline alkaloids
JPH03109384A (ja)	1991-05-09	（Ｓ）―４―ヒドロキシメチル―γ―ラクトンの製造方法
JP2876712B2 (ja)	1999-03-31	光学活性ピラノベンゾオキサジアゾール誘導体
WO1988000190A1 (fr)	1988-01-14	Derives optiquement actifs de glycidol
US5319089A (en)	1994-06-07	Process for the optical resolution of pyranobenzoxadiazole compounds
EP0884313B1 (fr)	2000-11-08	Procede de production de sulfonate de glycidyle
US4946974A (en)	1990-08-07	Optically active derivatives of glycidol
US5153338A (en)	1992-10-06	Optically active derivatives of glycidol
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US5084569A (en)	1992-01-28	Trioxy bicyclic compounds useful for preparing optically active carboxylic acids
JP2004224764A (ja)	2004-08-12	光学活性トランス−１，２−シクロヘキサンジカルボン酸誘導体の製造方法
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US5532364A (en)	1996-07-02	Enantiomerically pure 2-oxa-5,8-diazabicyclo[4.3.0]nonanes and process for their preparation
EP0217376B1 (fr)	1990-09-12	Procédé pour la fabrication des cétones aryliques alpha-haloalkylés optiquement actives
JPH02289563A (ja)	1990-11-29	ｏ―カルボキシピリジル―およびｏ―カルボキシキノリルイミダゾリノンの改良製造法
JPH02256650A (ja)	1990-10-17	ジカルボン酸モノエステルおよびその製造法
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