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Carbohydr Res. 2010 Jul 2;345(10):1366-70. doi: 10.1016/j.carres.2010.04.018. Epub 2010 Apr 22.

Double diastereoselection explains limitations in synthesizing mannose-containing beta-(1,3)-glucans.

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  • 1Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, Avenue du Général Leclerc, CS 50837, 35708 Rennes Cedex 7, France.


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 alpha-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.

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