A concise and practical stereoselective synthesis of ipragliflozin L-proline

Author:

Ma Shuai,Liu Zhenren,Pan Jing,Zhang Shunli,Zhou Weicheng

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.

Publisher

Beilstein Institut

Subject

Organic Chemistry

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