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阳离子钯(II)催化的糖基三氯乙酰亚胺酯的立体选择性糖基化反应。

Cationic palladium(II)-catalyzed stereoselective glycosylation with glycosyl trichloroacetimidates.

作者信息

Yang Jaemoon, Cooper-Vanosdell Colleen, Mensah Enoch A, Nguyen Hien M

机构信息

Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, USA.

出版信息

J Org Chem. 2008 Feb 1;73(3):794-800. doi: 10.1021/jo702436p. Epub 2008 Jan 10.

DOI:10.1021/jo702436p
PMID:18184010
Abstract

The development of a new method for stereoselective glycosylation with glycosyl trichloroacetimidate donors employing cationic palladium(II), Pd(CH(3)CN)(4)(BF(4))(2), is described. This process employs Pd(CH(3)CN)(4)(BF(4))(2) as an efficient activator, providing access to a variety of disaccharides and glycopeptides. This reaction is highly stereoselective and proceeds under mild conditions with low catalyst loading. Interestingly, this palladium catalysis directs beta-glucosylations in the absence of classical neighboring group participation.

摘要

描述了一种使用阳离子钯(II),即Pd(CH(3)CN)(4)(BF(4))(2),与糖基三氯乙酰亚胺酯供体进行立体选择性糖基化的新方法的开发。该过程使用Pd(CH(3)CN)(4)(BF(4))(2)作为高效活化剂,可用于制备多种二糖和糖肽。该反应具有高度的立体选择性,在温和条件下以低催化剂负载量进行。有趣的是,这种钯催化在没有经典邻基参与的情况下指导β-葡萄糖基化反应。

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