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Synthesis 2021; 53(14): 2435-2448
DOI: 10.1055/a-1440-9386
DOI: 10.1055/a-1440-9386
paper
Convergent Synthesis of Branched β-Glucan Tridecasaccharides Ready for Conjugation
We are grateful for financial support from the National Natural Science Foundation of China (Nos. 21672194 and 21977088), the National Natural Science Foundation of China-Shandong Joint Fund (No. U1906213), and the Natural Science Foundation of Shandong Province (No. ZR2018MB015).
Abstract
Structurally defined and pure oligosaccharides corresponding to β-glucans have attracted great attention because of their potential properties as immunostimulating agents and as antigens of vaccine candidates. We herein describe a convergent synthesis of ready-to-conjugate tridecasaccharides composed of a β-1,3-glucan nonasaccharide backbone and a β-1,6-glucan tetrasaccharide branch. The assembly was achieved by employing trichloroacetimidate glycosylations and features the gram-scale preparation of the nonasaccharide backbone and installation of the tetrasaccharide branch involving orthoester rearrangement to the glycoside.
Key words
β-glucans - glycosyl trichloroacetimidates - oligosaccharide synthesis - orthoester rearrangement - convergent synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1440-9386.
- Supporting Information
Publikationsverlauf
Eingereicht: 19. Februar 2021
Angenommen nach Revision: 16. März 2021
Accepted Manuscript online:
16. März 2021
Artikel online veröffentlicht:
12. April 2021
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