化学
转鼓
除氧
糖基
磺酰
立体选择性
立体专一性
组合化学
偶联反应
功能群
有机化学
催化作用
烷基
亲核细胞
聚合物
作者
Siyu Li,Yujuan Wang,Lei Zhong,Siyu Wang,Zhengli Liu,Yuanwei Dai,Yun He,Feng Zhang
出处
期刊:Organic Letters
[American Chemical Society]
日期:2022-03-25
卷期号:24 (13): 2463-2468
被引量:14
标识
DOI:10.1021/acs.orglett.2c00353
摘要
S-Glycosides have broad biological activities and serve as stable mimics of natural O-glycoside counterparts and thus are of great therapeutic potential. Herein we disclose an efficient method for the stereospecific synthesis of 1-thioglycosides via a boron-promoted reductive deoxygenation coupling reaction from readily accessible sulfonyl chlorides and glycosyl bromides. Our protocol features mild conditions and excellent functional group tolerance and stereoselectivity. The translational potential of this metal-free approach is demonstrated by the late-stage glycodiversification of natural products and drug molecules.
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