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Synthesis 2023; 55(05): 773-778
DOI: 10.1055/s-0041-1738428
DOI: 10.1055/s-0041-1738428
paper
Straightforward Synthesis of the Pentasaccharide Repeating Unit of the O-Antigenic Polysaccharide from the Enteropathogenic Escherichia coli O142
S.K.J. and P.S. thank the Bose Institute for financial support. This work was supported by the Science and Engineering Research Board (SERB), New Delhi (Project No. CRG/2019/000352 dated 23.01.2020) (A.K.M.).
Abstract
The pentasaccharide repeating unit rich in 2-acetamido sugars corresponding to the O-antigenic polysaccharide from enteropathogenic Escherichia coli (E. coli) has been synthesized as the p-methoxyphenyl glycoside in excellent yield using a sequential glycosylation strategy. Regioselective glycosylation, use of a single monosaccharide intermediate in multiple glycosylations, and use of thioglycosides as glycosyl donors in the presence of a combination of N-iodosuccinimide (NIS) and perchloric acid supported over silica (HClO4–SiO2) are key components of the synthetic strategy. All glycosylation reactions were high-yielding with excellent stereochemical outcome.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1738428.
- Supporting Information
Publication History
Received: 26 September 2022
Accepted after revision: 13 October 2022
Article published online:
17 November 2022
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