Dapagliflozin R-furanose

Dapagliflozin R-furanose is a stereospecific degradation impurity of dapagliflozin, characterized by a five-membered furanose ring substituting the native six-membered pyranose moiety. The compound retains the 1,5-dichloro-2,4-dihydroxybenzene core and chlorobenzylidene acetal linkage but exhibits altered glycosidic stereochemistry at the anomeric center. The R-configuration of the furanose ring introduces distinct conformational constraints, differentiating it from S-isomers and other process-related impurities. This species arises via acid-catalyzed retro-aldol fragmentation during stability studies. It functions as an HPLC reference standard for quantifying furanose-specific degradation pathways in dapagliflozin formulations.