A concise and practical stereoselective synthesis of ipragliflozin L-proline

Abstract

A concise and practical stereoselective synthesis of ipragliflozin L-proline was presented starting from 2-[(5-iodo-2-fluorophenyl)methyl]-1-benzothiophene and 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide without catalyst via iodine–lithium–zinc exchange. The overall yield was 52% in three steps and the product purity was excellent. Two key diastereomers were prepared with efficient and direct access to the α-C-arylglucoside.

Keywords

• arylzinc derivative
• β-C-arylglucoside
• diastereomer impurity
• ipragliflozin L-proline
• stereoselective synthesis