Synthesis of the Hexasaccharide Repeating Unit Corresponding to the Cell Wall O-Antigen of Providencia alcalifaciens O9:H8 Strain

Abstract

A straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Providencia alcalifaciens O9:H8 strain was achieved in very good yield by applying a stereo- and regioselective [4+2] block glycosylation strategy. The tetrasaccharide acceptor and disaccharide donor were synthesized by sequential stereo- and regioselective glycosylations. Thioglycoside and glycosyl trichloroacetimidate derivatives were used as glycosyl donors in the synthetic strategy. The glycosylation steps were high-yielding and gave satisfactory stereochemical outcomes.

Key words

carbohydrates - glycosylation - glycoside - oligosaccharide - synthesis

Publication History

Received: 25 August 2023

Accepted after revision: 04 October 2023

Article published online:
20 November 2023

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