Issue 49, 2024

Stereoselective synthesis of α-glycosyl azides: allyl glycosyl sulfones as radical precursors

Abstract

Despite their critical importance in drug development and biochemistry, efficiently synthesizing α-glycosyl azides has continued to pose significant challenges. In this report, we introduce a universal and practical radical reaction for the stereoselective synthesis of α-glycosyl azides using bench-stable allyl glycosyl sulfones as the donor. This method is characterized by its mild reaction conditions, high stereoselectivity, and extensive scope of glycosyl units. Moreover, the accessibility of several structurally complex drug–sugar conjugates underscores the practicality of our approach.

Graphical abstract: Stereoselective synthesis of α-glycosyl azides: allyl glycosyl sulfones as radical precursors

Supplementary files

Article information

Article type
Communication
Submitted
10 Apr 2024
Accepted
21 May 2024
First published
22 May 2024

Chem. Commun., 2024,60, 6288-6291

Stereoselective synthesis of α-glycosyl azides: allyl glycosyl sulfones as radical precursors

Y. Li, Y. Tian, D. Xie, Y. Wang and D. Niu, Chem. Commun., 2024, 60, 6288 DOI: 10.1039/D4CC01687D

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