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Studies on C ‐glycosides: XII. Stereoselective synthesis of C ‐aryl glucosides
Author(s) -
Cai MengShen,
Qiu DongXu
Publication year - 1989
Publication title -
acta chimica sinica english edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 0256-7660
DOI - 10.1002/cjoc.19890070413
Subject(s) - chemistry , anomer , anhydrous , stereoselectivity , aryl , lewis acids and bases , yield (engineering) , glycoside , catalysis , organic chemistry , lewis acid catalysis , medicinal chemistry , stereochemistry , alkyl , materials science , metallurgy
2,3,4,6‐Tetra‐ O ‐benzyl‐ D ‐glucopyranose 1‐α‐( p ‐nitrobenzoate) reacted with aryl ethers in the presence of Lewis acid to give β‐anomers stereoselectively in high yield, but reaction with 1,3‐ditrimethylsilyloxybenzene gave α‐anomer using BF 3 ·Et 2 O and β‐anomer using anhydrous AlCl 3 as catalyst.