Department of Pharmacy - Drug Sciences, University of Bari "A. Moro" Via E. Orabona 4, Bari 70125, Italy.
Department of Chemistry and Pharmacy, University of Sassari, Via Vienna 2, 07100, Sassari, Italy.
Org Biomol Chem. 2020 May 27;18(20):3893-3897. doi: 10.1039/d0ob00647e.
A synthesis of unprecedented and stable glycosyl sulfoximines is reported. The developed strategies represent the first example of highly stereoselective sulfoximine formation directly from thioglycosides. This synthetic protocol has been tested on several β-thioglycosides bearing different aromatics and alkyls as S-substituents, and bearing glucose, mannose and galactose as glycosyl units. The process has been extended to a lactose derived thioglycoside and to a glucose derived sulfenamide. The process was chemo- and stereoselective, and X-ray analysis confirmed the structure and provided stereochemical information on the configuration at the sulfur atom. A model for the stereochemical outcome is proposed based on the steric environment of the sulfide.
本文报道了一种前所未有的稳定糖基磺酰亚胺的合成方法。所开发的策略代表了直接从硫代糖苷高立体选择性形成磺酰亚胺的首例。该合成方案已在几种带有不同芳基和烷基作为 S-取代基的β-硫代糖苷以及带有葡萄糖、甘露糖和半乳糖作为糖基单元的糖苷上进行了测试。该方法已扩展到衍生自乳糖的硫代糖苷和衍生自葡萄糖的亚磺酰胺。该过程具有化学选择性和立体选择性，X 射线分析证实了结构，并提供了关于硫原子构型的立体化学信息。根据硫化物的空间环境，提出了一个立体化学结果的模型。
