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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 10: 3094 - 3111

DOI: https://doi.org/10.6023/cjoc202006005

Advances in the Synthesis of C-Glycosides from Glycals

  • Guo Zhenyan ,
  • Bai Jinhe ,
  • Liu Miao ,
  • Xiong Decai ,
  • Ye Xinshan
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  • State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191

Received date: 2020-06-05

  Revised date: 2020-07-02

  Online published: 2020-07-23

Supported by

Project supported by the National Key Research and Development Program of China (No. 2018YFA0507602), the National Natural Science Foundation of China (No. 21738001), and the National New Drug Innovation Major Project of China (No. 2019ZX09301106).

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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 . DOI: 10.6023/cjoc202006005

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