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

Han Ding, Jian Lyu, Xiao-Lin Zhang, Xiong Xiao () and Xue-Wei Liu ()
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Han Ding: Nanyang Technological University
Jian Lyu: Nanyang Technological University
Xiao-Lin Zhang: Nanyang Technological University
Xiong Xiao: Northwestern Polytechnical University (NPU)
Xue-Wei Liu: Nanyang Technological University

Nature Communications, 2023, vol. 14, issue 1, 1-12

Abstract: Abstract Catalytic glycosylation is a vital transformation in synthetic carbohydrate chemistry due to its ability to expediate the large-scale oligosaccharide synthesis for glycobiology studies with the consumption of minimal amounts of promoters. Herein we introduce a facile and efficient catalytic glycosylation employing glycosyl ortho−2,2-dimethoxycarbonylcyclopropylbenzoates (CCBz) promoted by a readily accessible and non-toxic Sc(III) catalyst system. The glycosylation reaction involves a novel activation mode of glycosyl esters driven by the ring-strain release of an intramolecularly incorporated donor-acceptor cyclopropane (DAC). The versatile glycosyl CCBz donor enables highly efficient construction of O-, S-, and N-glycosidic bonds under mild conditions, as exemplified by the convenient preparation of the synthetically challenging chitooligosaccharide derivatives. Of note, a gram-scale synthesis of tetrasaccharide corresponding to Lipid IV with modifiable handles is achieved using the catalytic strain-release glycosylation. These attractive features promise this donor to be the prototype for developing next generation of catalytic glycosylation.

Date: 2023
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DOI: 10.1038/s41467-023-39619-7

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