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The Journal of Organic Chemistry

The Journal of Organic Chemistry

IF: 3.3
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Weinreb Amide Approach to the Practical Synthesis of a Key Remdesivir Intermediate

Published:18 March 2021 DOI: 10.1021/acs.joc.0c02986 PMID: 33733767
Yuanchao Xie, Tianwen Hu, Yan Zhang, Daibao Wei, Wei Zheng, Fuqiang Zhu, Guanghui Tian, Haji A. Aisa*, Jingshan Shen*

Abstract

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.

Substances (3)

Related products
Procduct Name CAS Molecular Formula Supplier Price
Remdesivir 1809249-37-3 C27H35N6O8P 365 suppliers $10.00-$13340.00
2,3,5-Tri-O-benzyl-D-ribonolactone 55094-52-5 C26H26O5 311 suppliers $5.00-$1647.00
Methylmagnesium Bromide 75-16-1 CH3BrMg 303 suppliers $12.00-$4334.49

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