Photocatalyzed Decarboxylative Thio(seleno)etherification of Redox-Active Uronates Enables Synthesis of Rare Sugar Thio(seleno)glycosides

Organic Letters 2026

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Authors: Xinxin Zhang, Han Ding, Jinping Zhang, Chaomin Sun, Dongbo Cui, Ni Song, Peng Wang, Xue‐Wei Liu, Ming Li
DOI: 10.1021/acs.orglett.5c05122
Cited by: 0
References: 61

Abstract

Rare sugar-based thio(seleno)glycosides are synthetically and biologically important yet challenging-to-prepare synthons. We here present a novel approach to such constructs from readily available C -glycosides with photocatalyzed decarboxylative thio(seleno)etherification of redox-active uronates as the key transformation following a C1-to-C5 switch strategy. This protocol tolerates diverse substrates and various protecting groups, stereoselectively affording the desirable thio(seleno)glycosides in moderate-to-high yields. The power of this method is demonstrated by the successful assembly of a 1,7- S -linked trisaccharide composed of α- d - ido -heptopyranosyl units.

Fields of Study & Subjects

Carbohydrate Chemistry and Synthesis Sulfur-Based Synthesis Techniques Organoselenium and organotellurium chemistry

Publication details

Journal / source
Organic Letters
Volume
28
Issue
3
Pages
1036–1041
Publication date
8 January 2026
Language
EN