Synthesis of the sialic acid-containing tetrasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia coli O131 strain

Abstract

A concise synthetic strategy have been developed for the synthesis of the sialic acid-containing tetrasaccharide repeating unit of the cell wall O-antigen of Escherichia coli (E. coli) O131 strain using regio- and stereoselective (2 → 6)-α-glycosylations of judiciously protected sialic acid thioglycoside derivatives. Perchloric acid supported over silica (HClO4–SiO2) in combination with N-iodosuccinimide (NIS) has been used in the stereoselective activation of thioglycoside derivatives as well as used as a solid acid for the functional group modifications. Appropriate stereoselectivity was achieved in the glycosylation steps involved in the synthetic strategy.