Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Chemical Biology Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, P. R. China.
Org Lett. 2023 Jun 9;25(22):4177-4182. doi: 10.1021/acs.orglett.3c01484. Epub 2023 May 30.
A highly efficient, palladium-catalyzed glycosylation between 3,4--carbonate glycals and acid-labile oximes is disclosed. This approach features broad substrate scope, high functional group tolerance, and easy scalability, delivering glycosyl oximes in excellent yields with exclusive β-selectivity and retention of / geometries. The power of this method is demonstrated by a set of site-selective transformations of glycosylation products and late-stage glycodiversification of bioactive molecules. Overall, our strategy provides an efficient toolkit for facile access to valuable N-O-linked glycosides.
本文报道了一种高效、钯催化的 3,4--碳酸苷基与酸不稳定肟之间的糖苷化反应。该方法具有广泛的底物范围、高官能团容忍度和易于规模化的特点，以优异的收率和β选择性以及保留/几何构型提供糖苷肟。该方法的应用价值通过一系列糖苷化产物的选择性转化和生物活性分子的晚期糖基多样化得到了证明。总的来说，我们的策略为方便获得有价值的 N-O 连接的糖苷提供了一个有效的工具包。
