ONE-POT CONVERSION OF 1,2-DIOLS TO EPOXIDES - CONVENIENT PREPARATION OF METHYL 2,3-ANHYDRO-5-O-TRITYL-BETA-D-LYXOFURANOSIDE AND METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-MANNOPYRANOSIDE

被引:7
作者
MURTHY, VS [1 ]
GAITONDE, AS [1 ]
RAO, SP [1 ]
机构
[1] INDIAN INST CHEM TECHNOL,HYDERABAD 500007,INDIA
关键词
D O I
10.1080/00397919308009780
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tosyl chloride and sodium hydride are used to convert some 1,2-diols to epoxides in one-pot in enantiomerically/diastereomerically pure form.
引用
收藏
页码:285 / 289
页数:5
相关论文
共 50 条
[31]   REACTION OF METHYL 4,6-O-BENZYLIDENE-BETA-D-GLUCOPYRANOSIDE 2,3-BIS-CHLOROSULPHATE AND 6-O-TRITYL-CELLULOSE 2,3-BIS-CHLOROSULPHATE WITH DIMETHYLAMINE [J].
KRYLOVA, RG ;
SHASHKOV, AS ;
USOV, AI .
BIOORGANICHESKAYA KHIMIYA, 1991, 17 (05) :702-709
[32]   Convenient synthesis of 2,3-O-isopropylidene-5-thio-D-ribose and 5-thio-D-ribose;: synthesis of 1,4-anhydro-2,3-O-isopropylidene-α-D-ribopyranose and 1,4-anhydro-2,3-O-isopropylidene-5-thio-α-D-ribopyranose [J].
Fleetwood, A ;
Hughes, NA .
CARBOHYDRATE RESEARCH, 1999, 317 (1-4) :204-209
[33]   Convenient synthesis of 2,3-O-isopropylidene-5-thio-D-ribose and 5-thio-D-ribose; synthesis of 1,4-anhydro-2,3-O-isopropylidene-α-D-ribopyranose and 1,4-anhydro-2,3-O-isopropylidene-5-thio-α-D-ribopyranose [J].
Fleetwood, Andrea ;
Hughes, Neil A. .
Carbohydrate Research, 317 (01) :204-209
[34]   UNSATURATED CARBOHYDRATES .X. EPOXIDATIONS AND HYDROXYLATIONS OF 2,3-DIDEOXY-ALPHA-D-HEX-2-ENOPYRANOSIDES . 4 METHYL 4,6-DI-O-ACETYL-2,3-ANHYDRO-ALPHA-D-HEXOPYRANOSIDES [J].
FERRIER, RJ ;
PRASAD, N .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (04) :575-&
[35]   REACTION OF LITHIUM DIMETHYL CUPRATE WITH METHYL 2,3-ANHYDRO-5-DEOXY-ALPHA-D-RIBOFURANOSIDE - A NEW, CONVENIENT ROUTE FOR PREPARATION OF 2,5-DIDEOXY-2-C-METHYL-D-ARABINOFURANOSE DERIVATIVES [J].
YAMAMOTO, H ;
SASAKI, H ;
INOKAWA, S .
CARBOHYDRATE RESEARCH, 1982, 100 (MAR) :C44-C45
[36]   1,6-ANHYDRO-4-O-BENZYL-3-DEOXY-2-O-METHYL-BETA-D-RIBO-HEXOPYRANOSE AND 1,6-ANHYDRO-4-O-BENZYL-2-C-(2-CYANOETHYL)-2,3-DIDEOXY-BETA-D-RIBO-HEXOPYRANOSE [J].
GAINSFORD, GJ ;
FURNEAUX, RH ;
MASON, JM ;
TYLER, PC .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1995, 51 :2418-2421
[37]   CONVENIENT PREPARATION OF METHYL 4,6-DI-O-ACETYL-2,3-DIDEOXY-BETA-D-ERYTHRO-HEX-2-ENOPYRANOSIDE [J].
DEBOER, A ;
THANEL, CJ ;
WILSON, GA .
TETRAHEDRON LETTERS, 1972, (50) :5137-&
[38]   THE CRYSTAL-STRUCTURE OF METHYL 4,6-O-BENZYLIDENE-2,3-DIDEOXY-2-[2-(METHOXYCARBONYL)PHENYLAMINO]-3-NITRO-BETA-D-MANNOPYRANOSIDE [J].
CONTURO, TE ;
JEFFREY, GA .
CARBOHYDRATE RESEARCH, 1982, 104 (01) :33-40
[39]   IMPROVED SYNTHESIS OF METHYL 4,6-O-BENZYLIDENE-3-CYANO-2,3-DIDEOXY-ALPHA-D-ERYTHRO-HEX-2-ENOPYRANOSIDE AND METHYL 4,6-O-BENZYLIDENE-2,3-DIDEOXY-3-C-FORMYL-ALPHA-D-ERYTHRO-HEX-2-ENOPYRANOSIDE [J].
SPANEVELLO, RA ;
PELLEGRINET, SC .
SYNTHETIC COMMUNICATIONS, 1995, 25 (22) :3663-3670
[40]   BRANCH-CHAIN SUGARS - THE REACTION OF METHYL 2,3-ANHYDRO-5-O-BENZYL-D-RIBOFURANOSIDES WITH DIETHYLALUMINUM CYANIDE [J].
BOBEK, M ;
WATANABE, S .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1982, 183 (MAR) :10-CARB