Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen Pf 20, Hungary.
Carbohydr Res. 2012 Oct 1;360:8-18. doi: 10.1016/j.carres.2012.07.012. Epub 2012 Jul 25.
Se-glycosyl-isoselenuronium salts such as three and four which can be prepared in one high-yielding step from acetohalogeno sugars proved to be convenient starting materials for the syntheses of a variety of selenoglycosides. Reaction with (ar)alkyl halides proceeds under mild conditions, in short time, at room temperature to afford the corresponding selenoglycosides in good yields. Aryl halides react to appreciable extent only if bearing activating nitro groups on the aromatic ring. Reactions with acylating reagents such as acetic anhydride and benzoyl chlorides furnished anomeric selenoesters some of which were recently proposed as starting compounds for alternative selenoglycoside syntheses. Selenodisaccharides with two different monosaccharide units could also be prepared via reactions of glycosyl-isoselenuronium salts with monosaccharide derivatives bearing primary or secondary triflate groups.
Se-糖苷异硒脲盐，如三和四，可以从乙酰卤代糖一步高产制备，被证明是各种硒糖苷合成的方便起始原料。与（芳基）卤化物的反应在温和条件下，短时间内，在室温下进行，以良好的产率得到相应的硒糖苷。只有在芳环上带有活化的硝基时，芳基卤化物才会发生显著反应。与酰化试剂如乙酸酐和苯甲酰氯的反应得到了非端位硒酸酯，其中一些最近被提议作为替代硒糖苷合成的起始化合物。通过糖苷异硒脲盐与带有伯或仲三氟甲磺酸酯基的单糖衍生物的反应，也可以制备具有两个不同单糖单元的硒二糖。
