Journal
CARBOHYDRATE RESEARCH
Volume 345, Issue 10, Pages 1366-1370Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2010.04.018
Keywords
Glycosylation; Double diastereoselection; Match-mismatch effect; beta-(1,3)-Glucans
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It is known that 3-O-glycosylation of glucosidic acceptors bearing acyl groups in the 4 and 6 positions instead of a 4,6-O-benzylidene ring mainly affords a-glycosides. Described here is an unexpected stereochemical outcome for elongation at glucose O-3 of a beta-D-Glcp-(1 -> 3)-alpha-D-Manp disaccharide using peracetylated ethyl thioglucoside as a donor. This unexpected reaction was correlated with match-mismatch effects, as shown by efficient coupling of the same acceptor by a donor of L-configuration. (C) 2010 Elsevier Ltd. All rights reserved.
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