Choutka Jan, Kratochvíl Michal, Zýka Jakub, Pohl Radek, Parkan Kamil
Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Prague, Technická 5, 166 28, Prague, Czech Republic.
Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Gilead Sciences & IOCB Research Centre, Flemingovo Nám. 2, 166 10, Prague, Czech Republic.
Carbohydr Res. 2020 Oct;496:108086. doi: 10.1016/j.carres.2020.108086. Epub 2020 Jul 10.
A straightforward and scalable method for the synthesis of protected 2-hydroxyglycals is described. The approach is based on the chlorination of carbohydrate-derived hemiacetals, followed by an elimination reaction to establish the glycal moiety. 1,2-dehydrochlorination reactions were studied on a range of glycosyl chlorides to provide suitable reaction conditions for this transformation. Benzyl ether, isopropylidene and benzylidene protecting groups, as well as interglycosidic linkage, were found to be compatible with this protocol. The described method is operationally simple and allows for the quick preparation of 2-hydroxyglycals with other than ester protecting groups, providing a feasible alternative to existing methods.
本文描述了一种用于合成受保护的2-羟基糖烯的直接且可扩展的方法。该方法基于碳水化合物衍生的半缩醛的氯化反应，随后进行消除反应以形成糖烯部分。对一系列糖基氯化物进行了1,2-脱氯化氢反应研究，以提供该转化反应的合适条件。发现苄基醚、异亚丙基和亚苄基保护基以及糖苷间键与该方案兼容。所描述的方法操作简单，能够快速制备具有非酯保护基的2-羟基糖烯，为现有方法提供了一种可行的替代方案。
