Weinreb Amide Approach to the Practical Synthesis of a Key Remdesivir Intermediate
文献类型：期刊论文
| 作者 | Xie, Yuanchao1; Hu, Tianwen2,3; Zhang, Yan2,3; Wei, Daibao2,3; Zheng, Wei1,3; Zhu, Fuqiang4; Tian, Guanghui4; Aisa, Haji A.2,3; Shen, Jingshan1,3
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| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
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| 出版日期 | 2021-04-02 |
| 卷号 | 86期号:7页码:5065-5072 |
| ISSN号 | 0022-3263 |
| DOI | 10.1021/acs.joc.0c02986 |
| 通讯作者 | Aisa, Haji A.(haji@ms.xjb.zc.cn) ; Shen, Jingshan(shenjingshan@simm.ac.cn) |
| 英文摘要 | Currently, remdesivir is the first and only FDA-approved antiviral drug for COVID-19 treatment. Adequate supplies of remdesivir are highly warranted to cope with this global public health crisis. Herein, we report a Weinreb amide approach for preparing the key intermediate of remdesivir in the glycosylation step where overaddition side reactions are eliminated. Starting from 2,3,5-tri-O-benzyl-D-ribonolactone, the preferred route consisting of three sequential steps (Weinreb amidation, O-TMS protection, and Grignard addition) enables a high-yield (65%) synthesis of this intermediate at a kilogram scale. In particular, the undesirable PhMgCl used in previous methods was successfully replaced by MeMgBr. This approach proved to be suitable for the scalable production of the key remdesivir intermediate. |
| WOS关键词 | GS-5734 ; EBOLA |
| 资助项目 | National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002] ; 2020 ANSO Collaborative Research Project[ANSO-CR-SP2020-03] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| 出版者 | AMER CHEMICAL SOC |
| WOS记录号 | WOS:000637001800015 |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/297048]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Aisa, Haji A.; Shen, Jingshan |
| 作者单位 | 1.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China 2.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Reg, Urumqi 830011, Xinjiang, Peoples R China 3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 4.Topharman Shanghai Co Ltd, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Xie, Yuanchao,Hu, Tianwen,Zhang, Yan,et al. Weinreb Amide Approach to the Practical Synthesis of a Key Remdesivir Intermediate[J]. JOURNAL OF ORGANIC CHEMISTRY,2021,86(7):5065-5072. |
| APA | Xie, Yuanchao.,Hu, Tianwen.,Zhang, Yan.,Wei, Daibao.,Zheng, Wei.,...&Shen, Jingshan.(2021).Weinreb Amide Approach to the Practical Synthesis of a Key Remdesivir Intermediate.JOURNAL OF ORGANIC CHEMISTRY,86(7),5065-5072. |
| MLA | Xie, Yuanchao,et al."Weinreb Amide Approach to the Practical Synthesis of a Key Remdesivir Intermediate".JOURNAL OF ORGANIC CHEMISTRY 86.7(2021):5065-5072. |
入库方式： OAI收割
来源：上海药物研究所
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