Stereoselective Synthesis of Alkyl α‐D‐Glucopyranosides.

Abstract

Carbohydrates Carbohydrates U 0500Stereoselective Synthesis of Alkyl α-D-Glucopyranosides. -Glycosylation of β-D-glucosyl-N-allylthiocarbamates with alcohols, including hindered tertiary alcohols, using bromine as activator proceeds under mild conditions in a highly stereoselective fashion to afford the corresponding α-glucosides (III) (5 examples) in high yields. -(KASPRZYCKA, A.; PASTUCH, G.; CYGANEK, A.; SZEJA, W.; Pol.

Glycosylation of acid sensitive acceptors. Synthesis of (2,3-epoxy-1-propyl) glycosides

“…11 We have found that glycosyl N-allyl thiocarbamates react with glycidol in the presence of non-nucleophilic bases and halogens, pseudohalogens or some thiophilic metal salts as activators, with formation of the expected glycidyl glycosides. The reaction is highly stereoselective and leads practically exclusively to a-glycosides.…”