Synthesis of Salmonella enteritidis Antigenic Tetrasaccharide Repeating Unit by Employing Cationic Gold(I)-Catalyzed Glycosylation Involving Glycosyl N-1,1-Dimethylpropargyl Carbamate Donors

Abstract

Synthesis of an antigenic tetrasaccharide repeating unit of the Opolysaccharide of Salmonella enteritidis lipopolysaccharide has been accomplished. Those four monosaccharides were assembled stereoselectively by employing our recently developed cationic gold(I)-catalyzed glycosylation methodology involving various glycosyl N-1,1-dimethylpropargyl carbamate donors. The newly formed α-anomeric stereochemical configuration was controlled by the axial C2-OBz of the glycosyl donors via anchimeric assistance.