A concise and practical stereoselective synthesis of ipragliflozin L-proline

被引：8

作者：

Ma, Shuai ^{[1
]}

Liu, Zhenren ^{[1
]}

Pan, Jing ^{[1
]}

Zhang, Shunli ^{[1
]}

Zhou, Weicheng ^{[1
]}

机构：

[1] China State Inst Pharmaceut Ind, Shanghai Inst Pharmaceut Ind, Shanghai Key Lab Antiinfect, State Key Lab New Drug & Pharmaceut Proc, 285 Gebaini Rd, Shanghai 201203, Peoples R China

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 13卷

关键词：

arylzinc derivative; beta-C-arylglucoside; diastereomer impurity; ipragliflozin L-proline; stereoselective synthesis; TYPE-2; DIABETES-MELLITUS; 1ST GLOBAL APPROVAL; COTRANSPORTER; INHIBITOR; C-ARYL GLYCOSIDES; EMPAGLIFLOZIN;

D O I：

10.3762/bjoc.13.105

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and practical stereoselective synthesis of ipragliflozin L-proline was presented starting from 2-[(5-iodo-2fluorophenyl) methyl]-1-benzothiophene and 2,3,4,6-tetra-O-pivaloyl-a-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 a-C-arylglucoside.

引用

页码：1064 / 1070

页数：7

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