A mild and convenient method for the synthesis of reverse glycosyl fluorides 
(RGFs) has been developed that is based on the silver-promoted radical 
dehydroxymethylative fluorination of carbohydrates. A salient feature of the 
reaction is that furanoid and pyranoid carbohydrates furnish structurally 
diverse RGFs bearing a wide variety of functional groups in good to excellent 
yields. Intramolecular hydrogen atom transfer experiments revealed that the 
reaction involves an underexploited radical fluorination that proceeds via 
β-fragmentation of sugar-derived primary alkoxyl radicals. Structurally 
divergent RGFs were obtained by catalytic C-F bond activation, and our method 
thus offers a concise and efficient strategy for the synthesis of reverse 
glycosides by late-stage diversification of RGFs. The potential of this method 
is showcased by the preparation and diversification of sotagliflozin, leading to 
the discovery of a promising SGLT2 inhibitor candidate.