Nucleophilic displacements on a cyclic sulfamidate derived from allosamine: Application to the synthesis of thiooligosaccharides

被引:38
作者
Aguilera, B [1 ]
FernandezMayoralas, A [1 ]
机构
[1] CSIC,INST QUIM ORGAN,GRP CARBOHIDRATOS,E-28006 MADRID,SPAIN
关键词
D O I
10.1039/cc9960000127
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The cyclic sulfamidate of the allosamine derivative 11 is efficiently prepared by reaction with 1,1'-sulfuryl diimidazole; the regioselective opening of this compound by sulfur nucleophiles furnishes 3-thioglucosamine derivatives, useful intermediates in synthesis of thiooligosaccharides.
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页码:127 / 128
页数:2
相关论文
共 11 条
[1]   THE DIRECT SYNTHESIS OF THE CYCLIC SULPHAMIDATE OF (S)-PROLINOL - SIMULTANEOUS N-PROTECTION AND ACTIVATION TOWARDS NUCLEOPHILIC DISPLACEMENT OF OXYGEN [J].
ALKER, D ;
DOYLE, KJ ;
HARWOOD, LM ;
MCGREGOR, A .
TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :877-880
[2]   CYCLIC SULPHAMIDATES - NEW SYNTHETIC PRECURSORS FOR BETA-FUNCTIONALIZED ALPHA-AMINO-ACIDS [J].
BALDWIN, JE ;
SPIVEY, AC ;
SCHOFIELD, CJ .
TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :881-884
[3]   RETRACTED: OLIGOSACCHARIDE LIGANDS FOR NKR-P1 PROTEIN ACTIVATE NK CELLS AND CYTOTOXICITY (Retracted article. See vol. 500, pg. 492, 2013) [J].
BEZOUSKA, K ;
YUEN, CT ;
OBRIEN, J ;
CHILDS, RA ;
CHAI, WG ;
LAWSON, AM ;
DRBAL, K ;
FISEROVA, A ;
POSPISIL, M ;
FEIZI, T .
NATURE, 1994, 372 (6502) :150-157
[4]  
CHIARA JL, UNPUB
[5]   OLIGOSACCHARIDES STRUCTURALLY RELATED TO E-SELECTIN LIGANDS ARE INHIBITORS OF NEURAL CELL-DIVISION - SYNTHESIS, CONFORMATIONAL-ANALYSIS, AND BIOLOGICAL-ACTIVITY [J].
COTERON, JM ;
SINGH, K ;
ASENSIO, JL ;
DOMINGUEZDALDA, M ;
FERNANDEZMAYORALAS, A ;
JIMENEZBARBERO, J ;
MARTINLOMAS, M ;
ABADRODRIGUEZ, J ;
NIETOSAMPEDRO, M .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1502-1519
[6]  
DEFAYE J, 1991, STUDIES NATURAL PROD, V8
[7]   SELECTINS - INTERPRETERS OF CELL-SPECIFIC CARBOHYDRATE INFORMATION DURING INFLAMMATION [J].
LASKY, LA .
SCIENCE, 1992, 258 (5084) :964-969
[8]   SYNTHESIS OF OLIGOSACCHARIDES STRUCTURALLY RELATED TO E-SELECTIN LIGANDS [J].
SINGH, K ;
FERNANDEZMAYORALAS, A ;
MARTINLOMAS, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (06) :775-776
[9]   THE MITSUNOBU REACTION ON METHYL GLYCOSIDES AS ALCOHOL COMPONENT [J].
WEINGES, K ;
HAREMSA, S ;
MAURER, W .
CARBOHYDRATE RESEARCH, 1987, 164 :453-458
[10]   SYNTHESIS AND EVALUATION OF HOMOAZASUGARS AS GLYCOSIDASE INHIBITORS [J].
WONG, CH ;
PROVENCHER, L ;
PORCO, JA ;
JUNG, SH ;
WANG, YF ;
CHEN, LR ;
WANG, R ;
STEENSMA, DH .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1492-1501