A Facile Synthetic Approach for Alkyl α-Glycosides of Reducing Disaccharides

Abstract

Methanolysis and benzyl alcoholysis of β-cellobiosyl, or β-lactosyl, or β-maltosyl N, N-dimethyldithiocarbamate in the presence of mercuric chloride and cadmium carbonate were investigated. Methyl and benzyl glycosides formation proceeded in good yield under mild conditions, in which formation of α-anomer was always predominant over that of β-anomer : in methanolysis, the ratios of α-and β-anomers were about 4 : 1 and in benzyl alcoholysis, 2 : 1, respectively. Using this method methyl α-cellobioside, α-lactoside, and α-maltoside were synthesized. The procedure is a facile synthetic method for appropriate alkyl α-glycosides of reducing disaccharides.