A concise and practical stereoselective synthesis of ipragliflozin L-proline

A concise and practical stereoselective synthesis of ipragliflozin L-proline

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 st...

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Bibliographic Details
Main Authors: Shuai Ma, Zhenren Liu, Jing Pan, Shunli Zhang, Weicheng Zhou
Format: Article
Language:English
Published: Beilstein-Institut 2017-06-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
arylzinc derivative
β-C-arylglucoside
diastereomer impurity
ipragliflozin L-proline
stereoselective synthesis
Online Access:https://doi.org/10.3762/bjoc.13.105
Description
Summary: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.
ISSN:1860-5397

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