Dapagliflozin alpha isomerI

Dapagliflozin alpha isomer I is a stereoisomeric impurity of the antidiabetic parent drug dapagliflozin, arising from differential configuration at the C-4 position of the pyran ring. It retains the core structure of dapagliflozin, including a 4-chlorophenyl moiety, a 1,5-dihydro-1,2,4-oxadiazole scaffold, and a glucoside-like ester linkage. The alpha configuration introduces a distinct spatial orientation of the hydroxyl group at C-4, altering intermolecular interactions while preserving key pharmacophoric elements. This isomer is synthesized via partial racemization during API manufacturing and serves as a reference standard for HPLC-based impurity profiling in dapagliflozin formulations.