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Straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62

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Abstract

A straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62 was achieved in very good yield applying sequential glycosylation strategy. Successful regioselective glycosylation of the di-hydroxylated L-rhamnose moiety allowed achieving the desired compound in minimum number of synthetic steps. TEMPO catalyzed and [bis(acetoxy)iodo]benzene (BAIB) mediated late stage regioselective oxidation of a primary hydroxyl group into carboxylic acid was achieved in the hexasaccharide derivative. The glycosylation steps were high yielding with high stereochemical outcome. The desired hexasaccharide was obtained in 7% over all yield in fourteen steps starting from suitably functionalized monosaccharide intermediates.

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Data availability

The data used for the current study are available from the corresponding author upon reasonable request and approval by the principal investigator.

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Funding

This work was supported by grants from Science and Engineering Research Board, India (Project No. CRG/2019/000352 dated 23.01.2020) and Bose Institute. AR and PS thank CSIR, New Delhi for providing Junior and Senior Research Fellowships respectively.

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  1. Department of Chemical Science, Bose Institute, Block EN-80, Sector-V, Salt Lake, Kolkata, 700091, India

    Abhijit Rana, Pradip Shit & Anup Kumar Misra

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Conceptualization and writing-original draft: Anup Kumar Misra; Data curation, investigation and writing draft: Abhijit Rana and Pradip Shit; Methodology and formal analysis: Abhijit Rana and Pradip Shit; Resources: Abhijit Rana and Pradip Shit.

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Correspondence to Anup Kumar Misra.

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Rana, A., Shit, P. & Misra, A.K. Straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62. Glycoconj J 40, 449–459 (2023). https://doi.org/10.1007/s10719-023-10122-x

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