Highly Regio-/Stereoselective Synthesis of Carbohydrates with Unsaturated Glycosyl Donors under Mild Conditions

Abstract

Carbohydrates and their conjugates play important roles in life activities and drug development. Our group was committed to the general and effective glycosylation methods and their application in chemical biology using unsaturated glycosyl donors. In the past five years, we have reported several synthetic strategies with high stereoselectivity and milder conditions compared with previous works. In particular, high chemo-/regio- and stereoselective O-glycosylation, C-glycosylation and S-glycosylation could be achieved via palladium catalysis under open-air conditions at room temperature. In this Account, we will introduce our research progress in constructing four types of glycosides.

1 Introduction

2 Stereoselective Synthesis of O-Glycosides

3 Stereoselective Synthesis of C-Glycosides

4 Stereoselective Synthesis of N-Glycosides

5 Stereoselective Synthesis of S-Glycosides

6 Conclusion

Key words

glycosylation - transition metal catalysis - unsaturated glycosyl donors - stereoselectivity - carbohydrates

Publication History

Received: 30 April 2024

Accepted after revision: 18 June 2024

Accepted Manuscript online:
19 June 2024

Article published online:
10 July 2024

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