Switchable and Stereospecific C-Glycosylation Strategy via Formal Functional Group Deletion

Abstract

Carbohydrates constitute an important class of biologically relevant natural products. Among the synthetic glycomimetics, C-glycosides are particularly interesting due to their chemical and metabolic stability toward acidic and enzymatic hydrolysis at the anomeric position. The stereochemical outcomes of traditional methodologies to access C-glycosides rely heavily on substrate control. Herein, we report a novel synthetic strategy to access diverse C-glycosides with precise stereochemical control at the anomeric position via formal functional group deletion, where both α- and β-anomers of furanoses and pyranoses can be obtained as single stereoisomers. Additionally, the broad scope of heterocyclic C-glycosides obtained via this strategy further illustrates its potential for empowering future application in both chemical biology research and drug discovery.