Advances in the Synthesis of C-Glycosides from Glycals

doi:10.6023/cjoc202006005

Abstract

C-Glycosides are a class of carbohydrates with a variety of biological activities, and the construction of their unique C-C glycosidic bond is a hot and challenging topic in carbohydrate chemistry. The formation of new C-C bond from carbon-carbon double bond is a common strategy in organic chemistry. With the rapid development of ene-chemistry, great progress in the synthesis of C-glycosides from glycal donors containing 1,2-double bond has been made. In this review, the methods for the synthesis of C-glycosides based on glycals are summarized, including Ferrier I-type C-glycosylation, Heck-type C-glycosylation, C-glycosylation of 1-substituted glycals using transition metal-catalyzed coupling reaction, Michael-type C-glycosylation of 2-substituted glycals, and radical addition type C-glycosylation of glycals.

Key words: glycal, C-glycoside, C-glycosylation, carbohydrate

Cite this article

Guo Zhenyan, Bai Jinhe, Liu Miao, Xiong Decai, Ye Xinshan. Advances in the Synthesis of C-Glycosides from Glycals[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3094-3111.

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