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

Xinyu Gao; Keke Ren; Lijuan Ma; Nengzhong Wang; Nianyu Huang; Hui Yao

doi:10.1055/a-2348-2803

Synlett, Table of Contents

Synlett 2025; 36(09): 1179-1188
DOI: 10.1055/a-2348-2803

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Carbohydrate Chemistry in China

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

Authors

Xinyu Gao

^aHubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, P. R. of China
Keke Ren

^aHubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, P. R. of China
Lijuan Ma

^aHubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, P. R. of China
Nengzhong Wang∗

^aHubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, P. R. of China

^bHubei Three Gorges Laboratory, Yichang 443007, P. R. of China
Nianyu Huang ∗

^aHubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, P. R. of China

^bHubei Three Gorges Laboratory, Yichang 443007, P. R. of China
Hui Yao ∗

^aHubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, P. R. of China

^bHubei Three Gorges Laboratory, Yichang 443007, P. R. of China

Abstract

All articles of this category

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

Full Text

References

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