One-Pot Stereoselective Synthesis of 2,3,4-Unprotected β-N-Glycopyranosides from Glycals and Amines

被引：5

作者：

Gao, Jingyu ^{[1
]}

Li, Yi ^{[1
]}

Wang, Nengzhong ^{[1
]}

Li, Zhiyue ^{[1
]}

Huang, Nianyu ^{[1
]}

Yao, Hui ^{[1
]}

机构：

[1] China Three Gorges Univ, Coll Biol & Pharmaceut Sci, Hubei Key Lab Nat Prod Res & Dev, Key Lab Funct Yeast China Natl Light Ind, Yichang 443002, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 14期

基金：

湖北省教育厅重点项目; 中国国家自然科学基金;

关键词：

N-Glycosides; Tsuji-Trost amination; One-pot synthesis; Palladium catalysis; BETA-C-GLYCOSYLATION; N-GLYCOSYLATION; ARYLBORONIC ACIDS; O-GLYCOSYLATION; GLYCOSIDES; REARRANGEMENT; NUCLEOSIDES; AIR; AMPHIMEDOSIDES; PROGRESS;

D O I：

10.1002/adsc.202300211

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A one-pot synthesis of 2,3,4-unprotected & beta;-N-glycopyranosides from glycals and amines with exclusive & beta;-stereoselectivity under room temperature conditions is reported. This method was achieved via palladium-catalyzed Tsuji-Trost amination followed by dihydroxylation directly, tolerating anilines, heterocyclic aromatic amines, and N,O-dimethylhydroxylamine, especially the reaction of primary amines and glycals has not been reported before. Furthermore, the protocol was applied to modify clinical drugs (prazosin, imiquimod) and construct the analogue of the natural product amphimedoside A.

引用

页码：2350 / 2355

页数：6

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