HYDROLYSIS OF O-ISOPROPENYL GLUCOPYRANOSIDES INVOLVES C-PROTONATION AND ALKENYL ETHER CLEAVAGE AND EXHIBITS A KINETIC INFLUENCE OF ANOMERIC CONFIGURATION

被引:22
作者
CHENAULT, HK
CHAFIN, LF
机构
[1] Department of Chemistry and Biochemistry, University of Delaware, Newark
关键词
D O I
10.1021/jo00100a015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hydrolysis of O-isopropenyl alpha-glucopyranoside occurs by C-protonation and alkenyl ether (not glycosidic) C-O bond cleavage and proceeds in 10 mM salicylate buffer, at pH 3.0 and 25 degrees C, 4.5 times faster than the similar hydrolysis of its beta anomer.
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页码:6167 / 6169
页数:3
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