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Synthesis 2024; 56(07): 1139-1146
DOI: 10.1055/s-0040-1720095
DOI: 10.1055/s-0040-1720095
paper
Emerging Trends in Glycoscience
Expeditious Synthesis of the Hexasaccharide Repeating Unit of the Capsular Polysaccharide of Streptococcus pneumoniae Type 7A
This work was supported by SERB, New Delhi (Project No. CRG/2019/000352 dated 23.01.2020) (AKM).
Abstract
The hexasaccharide repeating unit corresponding to the capsular polysaccharide of Streptococcus pneumoniae type 7A has been synthesized in good yield using [3+2+1] block synthetic strategy. The synthetic strategy involved a number of challenging stereoselective glycosylation steps, which include β-selective glycosylation of l-rhamnosyl thioglycoside donor, α-selective glycosylations of 2-azido-2-deoxy-d-glucopyranosyl thioglycoside donor and d-galactopyranosyl donor together with the formation of β-glycoside of d-galactosamine moiety and α-glycoside of l-rhamnosyl moiety. Suitably functionalized thioglycosides have been used as glycosyl donors and a combination of N-iodosuccinimide (NIS) and trimethylsilyl trifluoromethanesulfonate (TMSOTf) has been used as glycosylation promoter.
Key words
carbohydrates - glycosylation - glycoside - oligosaccharide - synthesis - Streptococcus pneumoniaeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1720095.
- Supporting Information
Publication History
Received: 03 July 2023
Accepted after revision: 04 October 2023
Article published online:
08 November 2023
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