Dapagliflozin sugar dimerI

Dapagliflozin sugar dimer I is a dimeric byproduct formed via intermolecular condensation of two dapagliflozin-derived glucose moieties, linked through their anomeric centers via a methylene bridge. This compound retains the benzofuran scaffold of the parent drug but exhibits an extended sugar core with additional hydroxyl functionalities at C-2, C-3, and C-4 positions of each glucose unit. The dimerization introduces steric hindrance and altered hydrogen-bonding capacity compared to monomeric dapagliflozin. This impurity arises during synthetic processes involving glycosidic coupling under acidic conditions. It serves as an HPLC reference standard for quantifying process-related impurities in dapagliflozin active pharmaceutical ingredient batches.