Indium salts-catalyzed O and S-glycosylation of bromo sugar with benzyl glycolate: An unprecedented hydrogenolysis

Abstract

Various O and S-glycosyl esters and their corresponding acids are synthesized through a reaction of bromo sugar and benzyl glycolate in the presence of indium trichloride and indium tribromide as promoter. We discovered unprecedented catalytic effects of indium tribromide in glycosylation and hydrogenolysis in a one-pot operation. The sugar acid is a potential chiral auxiliary for the synthesis of biologically active compounds of diverse interests.