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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-?-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 ?-C-arylglucoside.

SUBMITTER: Ma S

PROVIDER: S-EPMC5480354 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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A concise and practical stereoselective synthesis of ipragliflozin L-proline.

Ma Shuai S Liu Zhenren Z Pan Jing J Zhang Shunli S Zhou Weicheng W

Beilstein journal of organic chemistry 20170601

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-<i>O</i>-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-<i>C</i>-arylglucoside. ...[more]

PMID: 28684985

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