Stereoselective Synthesis of 2,3-Diamino-2,3-dideoxyglycosides from 3-O-Acetyl-2-nitroglycals

被引：11

作者：

Wu, Xiaopei ^{[1
]}

Zheng, Zhichao ^{[1
]}

Wang, Liming ^{[1
]}

Xue, Yunxia ^{[1
]}

Liao, Jinxi ^{[1
]}

Liu, Hui ^{[1
]}

Liu, Deyong ^{[1
]}

Sun, Jian-Song ^{[1
]}

Zhang, Qingju ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, 99 Ziyang Ave, Nanchang 330022, Jiangxi, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 2022卷 / 26期

基金：

中国国家自然科学基金;

关键词：

2; 3-Diamino-2; 3-dideoxyglycosides; 2-Nitroglycal; Organocatalysis; Relay glycosylation; Stereoselectivity; O-SPECIFIC POLYSACCHARIDE; BORDETELLA-BRONCHISEPTICA; OXOCARBENIUM IONS; REAGENT SYSTEM; 2-NITROGLYCALS; GLYCOSYLATION; CHEMISTRY; SUBSTITUENT; CHAINS;

D O I：

10.1002/ejoc.202200519

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Nitroglycal is a widely used synthon for aminoglycosides synthesis. Herein, we report an efficient method for 2-nitroglycals synthesis using (Bu4NNO3)-Bu-n/Tf2O/DTBMP. Using 3-O-acetyl-2-nitroglycals as donors, a novel method for the construction of challenging 1,2-cis-2,3-diamino-2,3-dideoxyglycosidic linkages was established using 4-pyrrolidinopyridine (PPY) mediated relay glycosylation reaction. The method enjoys many features, including very mild reaction condition, excellent regio- and stereoselectivity, good to excellent yields and broad substrate scope.

引用

页数：5

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