Canagliflozin S-Furanose

Canagliflozin S-Furanose is a structurally related impurity derived from the parent SGLT2 inhibitor canagliflozin, characterized by a five-membered furanose ring in place of the native six-membered pyranose moiety. The S-configuration at the anomeric carbon and retention of the 1-(3-iodo-4-methoxyphenyl)-2-[(4-methyl-5-oxo-4H-furan-2-yl)methyl]ethyl phthalimide core distinguish its stereochemistry and glycosidic linkage. This furanosyl variant arises via ring contraction during synthetic pathways or thermal degradation, preserving key pharmacophoric elements while altering conformational flexibility. It serves as a critical HPLC reference standard for quantifying process-related furanosylation impurities in canagliflozin drug substance.