Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4

Abstract

A straightforward sequential synthetic strategy has been developed for the synthesis of a pentasaccharide repeating unit corresponding to the cell wall O-antigen of the Escherichia albertii O4 strain in very good yield with the desired configuration at the glycosidic linkages using thioglycosides and trichloroacetimidate derivatives as glycosyl donors and perchloric acid supported over silica (HClO4/SiO2) as a solid supported protic acid glycosyl activator. The expected configuration at the glycosidic linkages was achieved using a reasonable selection of protecting groups in the manosaccharide intermediates.

Keywords

• escherichia albertii o4
• glycosylation
• hclo4/sio2
• o-antigen
• pentasaccharide