3-Epi empagliflozin Impurity is a stereoisomer of empagliflozin, characterized by an inversion of configuration at the C-3 position of the glucosidic moiety. It retains the core 1,5-dihydroxy-2-methylpyrrolidin-3-yl scaffold and 4-chlorobenzyl substituent but exhibits altered glycosidic stereochemistry. The molecule contains multiple hydroxyl groups, an ether linkage, and a chloride moiety, contributing to its distinct chromatographic behavior. This impurity arises during synthetic processes due to partial epimerization at the anomeric center. It serves as a critical HPLC reference standard for quantifying stereoisomeric impurities in empagliflozin formulations.
On RequestC1COC[C@@H]1OC2=CC=C(C=C2)CC3=C(C=CC(=C3)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)Cl
InChI=1S/C23H27ClO7/c24-18-6-3-14(23-22(28)21(27)20(26)19(11-25)31-23)10-15(18)9-13-1-4-16(5-2-13)30-17-7-8-29-12-17/h1-6,10,17,19-23,25-28H,7-9,11-12H2/t17-,19-,20-,21+,22-,23+/m1/s1
OBWASQILIWPZMG-VUOLKEHKSA-N