Convenient Synthesis of the Branched Hexasaccharide Repeating Unit of the Cell Wall O-Antigen of Escherichia coli O80 Strain

Abstract

Chemical synthesis of a branched hexasaccharide corresponding to the cell wall O-antigen of Escherichia coli (E. coli) O80 strain has been achieved in very good yield with satisfactory stereochemical outcome around the glycosidic linkages by applying a regio- and stereoselective [4+2] block glycosylation strategy. The tetrasaccharide diol derivative was synthesized from suitably functionalized monosaccharide intermediates using sequential stereoselective glycosylations and the disaccharide thioglycoside donor was obtained applying a regio- and stereoselective orthogonal armed-disarmed glycosylation strategy using protected thioglycoside derivatives. A late-stage TEMPO and bis(acetoxy)iodobenzene (BAIB) mediated regioselective oxidation of the primary hydroxyl group of the protected hexasaccharide derivative to the carboxylic acid was achieved leaving secondary hydroxyl groups unaffected.

Key words

carbohydrates - glycosylation - glycoside - oligosaccharide - synthesis - Escherichia coli

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