Convergent synthesis of the tetrasaccharide repeating unit corresponding to the O-antigen of the verotoxin-producing Escherichia coli O176

A convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of the verotoxin producing E. coli O176 has been achieved in excellent yield adopting a [2 + 2] block glycosylation strategy. The β-D-mannosidic moiety of the tetrasaccharide was prepared from β-D-glucoside and α-D-galactosamine moiety was derived from D-galactal. The tetrasaccharide was synthesized as its 2-trimethylsilylethyl glycoside in excellent yield. All intermediate steps are high yielding.