INCIDENCE AND AVOIDANCE OF STEREOSPECIFIC 1,2-ETHYLTHIO GROUP MIGRATION DURING THE SYNTHESIS OF ETHYL 1-THIO-ALPHA-L-RHAMNOPYRANOSIDE 2,3-ORTHOESTER

被引：54
作者：
AUZANNEAU, FI [1 ]
BUNDLE, DR [1 ]
机构：
[1] NATL RES COUNCIL CANADA,INST BIOL SCI,OTTAWA K1A 0R6,ONTARIO,CANADA
来源：
CARBOHYDRATE RESEARCH | 1991年 / 212卷
关键词：
D O I：
10.1016/0008-6215(91)84041-C
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The 1,2-migration of an ethylthio group with inversion of configuration at the C-1 and C-2 atoms was observed during the attempted preparation of 2,3-orthoester derivatives of ethyl 1-thio-alpha-L-rhamnopyranoside. The rearrangement leading to the formation of methyl 2-thio-beta-L-glucopyranosides could be avoided by preparing the orthoester in DMF rather than in acetonitrile and by using a controlled amount of acid catalyst.
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页码：13 / 24
页数：12
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