A minimalist approach to stereoselective glycosylation with unprotected donors

Nature Communications
Kim Le Mai HoangXue-Wei Liu

Abstract

Mechanistic study of carbohydrate interactions in biological systems calls for the chemical synthesis of these complex structures. Owing to the specific stereo-configuration at each anomeric linkage and diversity in branching, significant breakthroughs in recent years have focused on either stereoselective glycosylation methods or facile assembly of glycan chains. Here, we introduce the unification approach that offers both stereoselective glycosidic bond formation and removal of protection/deprotection steps required for further elongation. Using dialkylboryl triflate as an in situ masking reagent, a wide array of glycosyl donors carrying one to three unprotected hydroxyl groups reacts with various glycosyl acceptors to furnish the desired products with good control over regioselectivity and stereoselectivity. This approach demonstrates the feasibility of straightforward access to important structural scaffolds for complex glycoconjugate synthesis.

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Citations

Feb 28, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Xiang ZhaoQian Wan
Jul 4, 2018·Chemical Reviews·Michael Martin Nielsen, Christian Marcus Pedersen
Jul 1, 2020·The Journal of Organic Chemistry·Mosidur Rahaman MollaRima Thakur
Feb 5, 2019·Journal of the American Chemical Society·Larissa Krasnova, Chi-Huey Wong
Jun 30, 2019·Organic Letters·Jing FangQian Wan
Feb 23, 2018·Accounts of Chemical Research·Wei-Lin LengXue-Wei Liu
Aug 21, 2018·Journal of the American Chemical Society·Sourav ChatterjeePeter H Seeberger
Sep 10, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Mingli LiuXin-Shan Ye

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Methods Mentioned

BETA
glycosylation
NMR
glucosylations
column chromatography

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