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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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

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spelling	doaj-5d494d5e3da2497ea12417aae43c358a2021-03-02T05:05:44ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-06-011311064107010.3762/bjoc.13.1051860-5397-13-105A concise and practical stereoselective synthesis of ipragliflozin L-prolineShuai Ma0Zhenren Liu1Jing Pan2Shunli Zhang3Weicheng Zhou4State Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, No. 285, Gebaini Rd., Shanghai 201203, P. R. of ChinaState Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, No. 285, Gebaini Rd., Shanghai 201203, P. R. of ChinaState Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, No. 285, Gebaini Rd., Shanghai 201203, P. R. of ChinaState Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, No. 285, Gebaini Rd., Shanghai 201203, P. R. of ChinaState Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, No. 285, Gebaini Rd., Shanghai 201203, P. R. of ChinaA 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.https://doi.org/10.3762/bjoc.13.105arylzinc derivativeβ-C-arylglucosidediastereomer impurityipragliflozin L-prolinestereoselective synthesis
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Shuai Ma Zhenren Liu Jing Pan Shunli Zhang Weicheng Zhou
spellingShingle	Shuai Ma Zhenren Liu Jing Pan Shunli Zhang Weicheng Zhou A concise and practical stereoselective synthesis of ipragliflozin L-proline Beilstein Journal of Organic Chemistry arylzinc derivative β-C-arylglucoside diastereomer impurity ipragliflozin L-proline stereoselective synthesis
author_facet	Shuai Ma Zhenren Liu Jing Pan Shunli Zhang Weicheng Zhou
author_sort	Shuai Ma
title	A concise and practical stereoselective synthesis of ipragliflozin L-proline
title_short	A concise and practical stereoselective synthesis of ipragliflozin L-proline
title_full	A concise and practical stereoselective synthesis of ipragliflozin L-proline
title_fullStr	A concise and practical stereoselective synthesis of ipragliflozin L-proline
title_full_unstemmed	A concise and practical stereoselective synthesis of ipragliflozin L-proline
title_sort	concise and practical stereoselective synthesis of ipragliflozin l-proline
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2017-06-01
description	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.
topic	arylzinc derivative β-C-arylglucoside diastereomer impurity ipragliflozin L-proline stereoselective synthesis
url	https://doi.org/10.3762/bjoc.13.105
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A concise and practical stereoselective synthesis of ipragliflozin L-proline

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