1. Palladium-Catalyzed Stereospecific S-Glycosylation by Allylic Substitution.
- Author
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Yanyan Wang, Zhen Cao, Nengzhong Wang, Mingguo Liu, Haifeng Zhou, Long Wang, Nianyu Huang, and Hui Yao
- Subjects
CHEMICAL decomposition ,GLYCOPEPTIDES ,STEREOSPECIFICITY ,DISACCHARIDES ,HYDROLYSIS - Abstract
S-Glycosides are considerably more stable toward chemical degradation and enzymatic hydrolysis than O-glycosides, and thioglyco-peptides/proteins also demonstrate critical bioactivities in the living system. However, the general and stereoselective synthetic strategies are still challenging. Herein, a versatile S-glycosylation approach was developed by palladium-catalyzed allylic substitution to form a- and ß-thioglycosides respectively under mild conditions. A wide range of substrates were tolerated to afford thioglycosides in a stereospecific manner with 70%-86% yields. This protocol also created the quick access to various S-linked disaccharides and glycopeptides. [ABSTRACT FROM AUTHOR]
- Published
- 2023
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