Zhong Lei, Wang Qunliang, Wang Yujuan, Cheng Yiyang, Xiong Yimeng, Peng Haibo, Zhou Zhen, He Yun, Dai Yuanwei
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, P. R. China.
Chongqing Institute of Green and Intelligent Technology, Chinese Academy of Sciences, Chongqing 400714, P. R. China.
Chem Commun (Camb). 2023 Oct 26;59(86):12907-12910. doi: 10.1039/d3cc04063a.
Glycosylation is an important strategy to improve the druggability of lead compounds. Here, we present a palladium-catalysed stereospecific -glycosylation of sulfonamides. This approach stands out with wide substrate scope, high functional group tolerance, and easy scalability, furnishing a broad spectrum of densely functionalized β--glycosyl sulfonamides with good efficiency and exceptional regio-/stereoselectivity. Diverse drug-like glycosulfonamido scaffolds have been constructed a late-stage diversification strategy and various facile synthetic transformations of the products. Collectively, the established protocol provides a valuable tool for efficiently preparing glycosyl sulfonamides to facilitate drug discovery.
糖基化是提高先导化合物成药性的重要策略。在此，我们展示了一种钯催化的磺酰胺的立体特异性β-糖基化反应。该方法具有底物范围广、官能团耐受性高和易于放大的特点，能够高效地提供一系列具有良好区域/立体选择性的高度官能化的β-糖基磺酰胺。通过后期多样化策略和产物的各种简便合成转化，构建了多种类药物糖基磺酰胺支架。总体而言，所建立的方案为高效制备糖基磺酰胺以促进药物发现提供了一个有价值的工具。
