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糖醛的立体选择性电-2-脱氧糖基化反应。

Stereoselective Electro-2-deoxyglycosylation from Glycals.

机构信息

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191, China.

Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 27 Shanda Nanlu, Jinan, Shandong, 250100, China.

出版信息

Angew Chem Int Ed Engl. 2020 Aug 24;59(35):15204-15208. doi: 10.1002/anie.202006115. Epub 2020 Jun 15.

Abstract

We report a novel and highly stereoselective electro-2-deoxyglycosylation from glycals. This method features excellent stereoselectivity, scope, and functional-group tolerance. This process can also be applied to the modification of a wide range of natural products and drugs. Furthermore, a scalable synthesis of glycosylated podophyllotoxin and a one-pot trisaccharide synthesis through iterative electroglycosylations were achieved.

摘要

我们报告了一种新型的、高度对映选择性的糖基化反应,该反应从糖醛出发。该方法具有出色的对映选择性、广泛的适用范围和官能团容忍性。此过程还可应用于多种天然产物和药物的修饰。此外,还实现了糖苷化鬼臼毒素的可规模化合成以及通过迭代电糖基化一锅法合成三糖。

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