Synthesis of the Tetrasaccharide Repeating Unit Corresponding to the O-Antigen of Providencia alcalifaciens O7:H7 Strain

Abstract

Synthesis of the tetrasaccharide corresponding to the O-antigen of Providencia alcalifaciens O7:H7 strain was achieved in satisfactory yield by applying a stereoselective glycosylation strategy. Stereoselective incorporation of β-l-rhamnose, α-d-glucosamine and α-d-glucose moieties in the tetrasaccharide was achieved in very good yield. The d-glucuronic acid moiety in the tetrasaccharide was achieved by late-stage TEMPO–bis(acetoxy)iodobenzene (BAIB)-mediated regioselective oxidation of the primary hydroxyl group of the d-glucose moiety. Thioglycosides were used as glycosyl donors in the presence of a combination of N-iodosuccinimide (NIS) and triflic acid (TfOH) as thiophilic promoter.

Key words

carbohydrates - glycosylation - glycosides - oligosaccharides - oxidation - synthesis

Publication History

Received: 05 December 2024

Accepted after revision: 23 December 2024

Article published online:
10 February 2025

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