Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

Beilstein Journal of Organic Chemistry
Yuichi YoshimuraNoriaki Minakawa

Abstract

To synthesize nucleoside and oligosaccharide derivatives, we often use a glycosylation reaction to form a glycoside bond. Coupling reactions between a nucleobase and a sugar donor in the former case, and the reaction between an acceptor and a sugar donor of in the latter are carried out in the presence of an appropriate activator. As an activator of the glycosylation, a combination of a Lewis acid catalyst and a hypervalent iodine was developed for synthesizing 4'-thionucleosides, which could be applied for the synthesis of 4'-selenonucleosides as well. The extension of hypervalent iodine-mediated glycosylation allowed us to couple a nucleobase with cyclic allylsilanes and glycal derivatives to yield carbocyclic nucleosides and 2',3'-unsaturated nucleosides, respectively. In addition, the combination of hypervalent iodine and Lewis acid could be used for the glycosylation of glycals and thioglycosides to produce disaccharides. In this paper, we review the use of hypervalent iodine-mediated glycosylation reactions for the synthesis of nucleosides and oligosaccharide derivatives.

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Citations

May 4, 2021·Organic Letters·Rion MaedaYuichi Yoshimura
Jun 17, 2020·The Journal of Organic Chemistry·Lucien CaspersBoris Johannes Nachtsheim

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Methods Mentioned

BETA
glycosylation
silica
glycosidation

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