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Current Organic Chemistry

Author(s): Nan Jiang , Zhengliang Wu, Youxian Dong, Xiaoxia Xu, Xiaxia Liu and Jianbo Zhang*

DOI: 10.2174/1385272824666200130111142

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Progress in the Synthesis of 2,3-unsaturated Glycosides

Page: [184 - 199] Pages: 16

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Abstract

The substitution reaction of glycal (1,2-unsaturated cyclic carbohydrate derivative) at C1 by allyl rearrangement in the presence of a catalyst is called Ferrier type-I rearrangement. 2,3-Unsaturated glycosides are usually obtained from glycals through Ferrier type-I rearrangement, and their potential biological activities have gradually attracted widespread attention of researchers. This review summarizes recent advances (2009- present) in the application of various types of catalysts to Ferrier type-I rearrangement reactions, including their synthesis, mechanism, and application of 2, 3-unsaturated glycosides.

Keywords: Synthesis, 2, 3-unsaturated glycoside, ferrier type-I rearrangement, catalyst, mechanism, application, bioactive.

Graphical Abstract

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