Synthesis of selenoglycosides and selenium linked disaccharides using reductive cleavage of diselenides

Abstract

Reduction of diselenides using a combination of hydrazine monohydrate and potassium hydroxide (KOH) followed by the treatment of the selenolate ions generated in situ with glycosyl halides under a one-pot, two-step phase transfer reaction condition resulted in the formation of beta-selenoglycosides in excellent yield. In addition, selenium linked disaccharide derivatives with beta-glycosidic linkages were also prepared by the reductive cleavage of diglycosyl diselenide derivatives in very good yield. The reaction condition is non-hazardous and high yielding for scaling up.