Weinreb Amide Approach to the Practical Synthesis of a Key Remdesivir Intermediate
文献类型:期刊论文
作者 | Xie, Yuanchao; Hu, Tianwen; Zhang, Yan; Wei, Daibao; Zheng, Wei; Zhu, Fuqiang; Tian, Guanghui; Aisa, Haji A![]() |
刊名 | The Journal of organic chemistry
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出版日期 | 2021 |
卷号 | 86期号:7页码:5065-5072 |
ISSN号 | 1520-6904 |
DOI | 10.1021/acs.joc.0c02986 |
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. |
源URL | [http://ir.xjipc.cas.cn/handle/365002/7810] ![]() |
专题 | 新疆理化技术研究所_省部共建新疆特有药用资源利用重点实验室 新疆理化技术研究所_资源化学研究室 |
作者单位 | 1.Topharman Shanghai Co., Ltd., No. 388 Jialilue Road, Zhangjiang Hitech Park, Shanghai 201203, P. R. China 2.University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, P. R. China 3.Key Laboratory of Plant Resources and Chemistry in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, South Beijing Road 40-1, Urumqi, Xinjiang 830011, P. R. China 4.Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. 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]. The 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.The 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".The Journal of organic chemistry 86.7(2021):5065-5072. |
入库方式: OAI收割
来源:新疆理化技术研究所
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