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Synthesis 2024; 56(10): 1648-1656
DOI: 10.1055/s-0042-1751559
paper

Convenient Synthesis of Hexa- and Pentasaccharide Repeating Units Corresponding to the O-Polysaccharides of Acinetobacter baumannii O7 and Acinetobacter baumannii O10 Strains

Samim Sahaji
,
Puja Bag
,
Anup Kumar Misra∗
S.S. thanks the University Grants Commission (UGC-MANF), India for a senior research fellowship. P.B. thanks University Grants Commission, India for a junior research fellowship. This work was supported by the Bose Institute, Kolkata (A.K.M.).
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Abstract

The synthesis of the hexa- and pentasaccharide repeating units of the cell wall O-polysaccharides of Acinetobacter baumannii O7 and O10 strains, respectively, has been achieved in very good yield using [4+2] and [4+1] block glycosylation strategies. The p-methoxybenzyl (PMB) group was used as an in situ removable protecting group, which was removed after glycosylation in the same pot by tuning the reaction condition. A challenging β-l-rhamnopyranosyl linkage was constructed using ‘armed-disarmed glycosylation’ conditions by the influence of a remotely located, H-bond mediating, picolinoyl group in the glycosyl donor. A d-mannosamine intermediate was prepared from d-glucose using minimum reaction steps. The hexa- and pentasaccharide were achieved as their p-methoxyphenyl (PMP) glycosides.

Key words

carbohydrates - glycosylation - glycoside - oligosaccharide - synthesis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751559.
  • Supporting Information


Publication History

Received: 01 January 2024

Accepted after revision: 26 January 2024

Article published online:
14 February 2024

© 2024. Thieme. All rights reserved

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