Double diastereoselection explains limitations in synthesizing mannose-containing beta-(1,3)-glucans. - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Carbohydrate Research Année : 2010

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

Résumé

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.

Domaines

Chimie organique

Dates et versions

hal-00759103 , version 1 (30-11-2012)

Identifiants

Citer

Balla Sylla, Karine Descroix, Christophe Pain, Cedric Gervaise, Frank Jamois, et al.. Double diastereoselection explains limitations in synthesizing mannose-containing beta-(1,3)-glucans.. Carbohydrate Research, 2010, 345 (10), pp.1366-70. ⟨10.1016/j.carres.2010.04.018⟩. ⟨hal-00759103⟩
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