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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...
| Autores principales: | , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2017
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5480354/ https://www.ncbi.nlm.nih.gov/pubmed/28684985 http://dx.doi.org/10.3762/bjoc.13.105 |
| _version_ | 1783245280916799488 |
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| author | Ma, Shuai Liu, Zhenren Pan, Jing Zhang, Shunli Zhou, Weicheng |
| author_facet | Ma, Shuai Liu, Zhenren Pan, Jing Zhang, Shunli Zhou, Weicheng |
| author_sort | Ma, Shuai |
| collection | PubMed |
| 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. |
| format | Online Article Text |
| id | pubmed-5480354 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2017 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-54803542017-07-06 A concise and practical stereoselective synthesis of ipragliflozin L-proline Ma, Shuai Liu, Zhenren Pan, Jing Zhang, Shunli Zhou, Weicheng Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2017-06-01 /pmc/articles/PMC5480354/ /pubmed/28684985 http://dx.doi.org/10.3762/bjoc.13.105 Text en Copyright © 2017, Ma et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
| spellingShingle | Full Research Paper Ma, Shuai Liu, Zhenren Pan, Jing Zhang, Shunli Zhou, Weicheng A concise and practical stereoselective synthesis of ipragliflozin L-proline |
| title | 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_short | A concise and practical stereoselective synthesis of ipragliflozin L-proline |
| title_sort | concise and practical stereoselective synthesis of ipragliflozin l-proline |
| topic | Full Research Paper |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5480354/ https://www.ncbi.nlm.nih.gov/pubmed/28684985 http://dx.doi.org/10.3762/bjoc.13.105 |
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