A facile preparation of alkyl α-glycosides of the methyl ester of N-acetyl-D-neuraminic acid

Abstract

The reaction of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,5-trideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate with primary and secondary alcohols in the presence of silver salicylate affords, after O-deacetylation, stereo-specifically the corresponding methyl (alkyl 5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onates. The preparation of methyl(neopentyl 5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate in benzene solution shows that this glycosylation can be carried out in an inert solvent.