Canagliflozin R-Furanose

Canagliflozin R-Furanose is a stereoisomeric impurity arising from the pyranose-to-furanose ring tautomerism of the parent SGLT2 inhibitor. It features a five-membered furanose ring with R-configuration at the anomeric center, retaining the 4-chlorophenyl, 5-(hydroxymethyl)furan-2-yl, and trifluoromethyl-substituted piperazine core. The compound exhibits altered glycosidic stereochemistry compared to the 1C-pyranose form of canagliflozin, with hydroxyl groups at C-2 and C-3 in axial/equatorial orientations. This impurity is generated under acidic stress conditions and serves as a reference standard for HPLC method validation to quantify tautomerism-derived degradation pathways.