C-glycosyl compounds offer exceptional in vivo stability. They are extensively investigated as drug candidates and can facilitate chemical biology studies. Previous synthetic methods exhibit various limitations with respect to the scope of sugars and coupling partners. The development of a redox auxiliary enables a cross-coupling method to prepare C-aryl and acyl glycosides, including nucleosides, from glycosyl esters. Activation of the carbohydrate substrates leverages dihydropyridine as a leaving group to generate a glycosyl radical upon photo-induced electron transfer. The convenient preparation of glycosyl esters and their stability exemplifies the potential of this method in medicinal chemistry.

Photoredox catalytic C-glycosylation of glycosyl esters

ACS Fall 2021

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.