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Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl *ortho*-2,2-dimethoxycarbonylcyclopropylbenzoate donors

Chemistry

Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl *ortho*-2,2-dimethoxycarbonylcyclopropylbenzoate donors

H. Ding, J. Lyu, et al.

This groundbreaking research by Han Ding, Jian Lyu, Xiao-Lin Zhang, Xiong Xiao, and Xue-Wei Liu unveils a novel catalytic glycosylation method using glycosyl *ortho*-2,2-dimethoxycarbonylcyclopropylbenzoates, facilitated by a scandium(III) catalyst. The study highlights an innovative activation mode that efficiently constructs diverse glycosidic bonds, paving the way for advanced oligosaccharide synthesis.

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Playback language: English
Abstract
This paper introduces a facile and efficient catalytic glycosylation employing glycosyl *ortho*-2,2-dimethoxycarbonylcyclopropylbenzoates (CCBz) promoted by a scandium(III) catalyst. The glycosylation reaction involves a novel activation mode driven by ring-strain release of an intramolecular donor-acceptor cyclopropane (DAC). The versatile glycosyl CCBz donor enables efficient construction of O-, S-, and N-glycosidic bonds under mild conditions, demonstrated by the synthesis of chitooligosaccharide derivatives and a gram-scale synthesis of a Lipid IV tetrasaccharide.
Publisher
Nature Communications
Published On
Jul 07, 2023
Authors
Han Ding, Jian Lyu, Xiao-Lin Zhang, Xiong Xiao, Xue-Wei Liu
Tags
catalytic glycosylation
scandium(III) catalyst
glycosyl CCBz donor
O-glycosidic bonds
chitooligosaccharides
intramolecular donor-acceptor cyclopropane
Lipid IV tetrasaccharide

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