Dapagliflozin S-Furanose

Dapagliflozin S-Furanose is a degradation byproduct of dapagliflozin, characterized by a tetrahydrofuran ring linked via a glycosidic bond to a chloro-substituted benzodioxole core. The compound retains the parent drug’s stereochemistry at the C-1 position but exhibits reduced ring saturation, replacing the pyranose moiety with a furanose structure. This structural alteration introduces additional oxygen heteroatoms and alters hydrogen bonding capacity, impacting solubility and chromatographic behavior. The molecule contains three stereocenters, including the S-configuration at the furanose junction, and retains the 4-chlorophenyl substituent critical for SGLT2 binding. It serves as an HPLC reference standard for quantifying process-related impurities in dapagliflozin formulations.