Synthesis of Remdesivir by Direct Lithiation of Pyrrolo[2,1-f][1,2,4]triazine Derivatives Enabled C-Glycosylation,European Journal of Organic Chemistry

当前位置： X-MOL 学术 › Eur. J. Org. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Synthesis of Remdesivir by Direct Lithiation of Pyrrolo[2,1-f][1,2,4]triazine Derivatives Enabled C-Glycosylation
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2023-04-28 , DOI: 10.1002/ejoc.202300197
Chao Xu ₁ , Yuhan Hu ₂ , Yong He ₃ , Zhigang Hu ₃ , Shikuo Li ₄ , Hui Zhang ₅ , Fangzhi Huang ₆ , Fenglian Zhang ₂ , yuelei Chen ₇

Affiliation

A 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.

中文翻译：

吡咯并[2,1-f][1,2,4]三嗪衍生物直接锂化合成瑞德西韦 C-糖基化

只需利用 C-9 上独特的 σ 酸性，即可在N -Boc-吡咯并[2,1-f][1,2,4]三嗪上实现直接和区域选择性的锂化。从这一发现出发，C-糖苷形成、氰化和整体脱保护步骤构成了 GS-441524 最有效的合成方法之一。此外，用苯基硼酸对 GS-441524 进行瞬时保护，促进了瑞德西韦的强大一锅合成。

更新日期：2023-04-28

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11