Synthesis of β-D-talopyranosides and β-D-mannopyranosides via intramolecular nucleophilic substitution

Abstract

The selective and efficient syntheses of β-D-talopyranosides and β-D-mannopyranosides were achieved from β-D-galactopyranosides and β-D-glucopyranosides, respectively, that carry a benzoyl group at O-3 and a triflyl group at O-2. The transformation was performed in the presence of an alcohol via intramolecular nucleophilic attack of the benzoyl group with inversion of configuration at C-2 that provided, first, the formation of the corresponding 2,3-(alkyl orthobenzoates) of the desired β-D-talopyranosides or β-D-mannopyranosides, followed by acidic opening of the cyclic orthoesters.