A convenient preparation of glycosyl sulfoxides and its application to the synthesis of Salidroside epimer

被引：4

作者：

Wang, Qing ^{[1
]}

Wei, Xiong ^{[1
]}

Liao, Kaijun ^{[1
]}

Li, Hui ^{[1
]}

Meng, Xiangbao ^{[1
]}

Li, Zhongjun ^{[1
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, Dept Biol Chem, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 21期

基金：

中国国家自然科学基金;

关键词：

Glycosyl sulfoxides; Aqueous H2O2; Oxidation; 1,2-cis glycosidic bond; Salidroside epimer; BETA-MANNOPYRANOSIDES; ANOMERIC SULFOXIDES; VERSATILE REAGENTS; HYDROGEN-PEROXIDE; SULFIDES; OXIDATION; EFFICIENT; DONORS; COMPLETION; ACTIVATION;

D O I：

10.1016/j.tetlet.2016.04.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and green approach for the preparation of glycosyl sulfoxides utilizing 30% aqueous H2O2 in phenol or acetic acid is described. Advantages include relatively mild conditions, high chemoselectivity, and good tolerance to a wide range of protective groups. Furthermore, the epimer of Salidroside containing one 1,2-cis glycosidic bond was synthesized in three steps in 90.1% overall yield using glucopyranosyl sulfoxide as the glycosyl donor. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2277 / 2279

页数：3

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