Work

Visible-light-promoted direct desulfurization of glycosyl thiols to access C-glycosides

Year: 2024

Type: article

Abstract: C-Glycosides are essential for the study of biological processes and the development of carbohydrates-based drugs. Despite tremendous hurdles, glycochemists have often fantasized of the efficient, highly stereoselective synthesis of C-glycosides with the shortest steps under mild conditions. Herein, we report a desulfurative radical protocol to synthesize C-alkyl glycosides and coumarin C-glycosides under visible-light induced conditions without the need of an extra photocatalyst, in which stable and readily available glycosyl thiols that could be obtained in two or three steps from native sugars are activated in situ by pentafluoropyridine. The benefits of this procedure include high stereoselectivity, broad substrates scope, and easily handle. Mechanistic studies indicated that the in situ produced tetrafluoropyridyl S-glycosides formed key EDA complexes with Hantzsch ester (for C-alkyl glycosides) or Et3N (for coumarin C-glycosides), which upon irradiation of visible light, triggered a cascade of glycosyl radical process to access C-glycosides smoothly.

Source: Nature Communications

DOI: 10.1038/s41467-024-53563-0

Authors: Demeng Xie, Wei Zeng, Jian Yang, Xiaofeng Ma

Institutions: Chinese Academy of Sciences, Chengdu Institute of Biology, University of Chinese Academy of Sciences

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $6,790

Funders: National Natural Science Foundation of China, Chinese Academy of Sciences, China Postdoctoral Science Foundation