CONVERSION OF BENZYL 3-O-BENZOYL-4,6-O-BENZYLIDENE-BETA-D-GALACTOPYRANOSIDE INTO 2-BENZOATE BY ACYL MIGRATION

被引:63
作者
CHITTENDEN, GJ
BUCHANAN, JG
机构
[1] Microbiological Chemistry Research Laboratory, Department of Organic Chemistry, The University, Newcastle upon Tyne
关键词
D O I
10.1016/S0008-6215(00)80580-7
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
Benzoylation of benzyl 4,6-O-benzylidene-β-d-galactopyranoside (1) with one equivalent of benzoyl chloride in pyridine-dichloromethane solution yields preferentially the 3-benzoate 3. Under alkaline conditions, benzoate 3 can be converted, in high yield, into the 2-benzoate 5, thus providingg an example of acyl migration towards C-1. © 1969.
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页码:379 / +
页数:1
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