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
收藏
页码：2277 / 2279
页数：3
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