Synthesis of Remdesivir by Direct Lithiation of Pyrrolo[2,1‐f][1,2,4]triazine Derivatives Enabled C‐Glycosylation

Author:

Xu Chao1,Hu Yu‐Han2,He Yong3,Hu Zhigang3,Li Shikuo1ORCID,Zhang Hui1,Huang Fangzhi1ORCID,Zhang Feng‐Lian2,Chen Yue‐Lei3ORCID

Affiliation:

1. Anhui University Chemistry & Chemical Engineering Anhui University 230601 Hefei Anhui P. R. China

2. Hefei National Laboratory for Physical Sciences at the Microscale Center for Excellence in Molecular Synthesis of CAS Department of Chemistry University of Science and Technology of China 230601 Hefei Anhui P. R. China

3. Nature Pharmaceutical (Anhui) Co. Ltd. 4th floor, 6# building, 8# Huangguan Road, Anqing Hi-Tech Development District 246000 Anqing Anhui province P. R. China

Abstract

AbstractA direct and regioselective lithiation was realized on N‐Boc‐pyrrolo[2,1‐f][1,2,4]triazine, simply utilizing the distinct sigma‐acidity on C‐9. Starting from this enabling discovery, C‐glycoside formation, cyanation, and global deprotection steps constitute one of the most efficient syntheses of GS‐441524. Furthermore, transient protection was applied on GS‐441524 with phenyl boronic acid, which facilitated a powerful one‐pot synthesis of remdesivir.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

Cited by 1 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Preparation of bicyclo[1.1.1]pentane-derived nucleoside analogues;Nucleosides, Nucleotides & Nucleic Acids;2023-06-04

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