Gu Jiamin, Chen Tong, Wang Qifang, Chen Tieyu, Ling Chang-Chun
Alberta Glycomics Centre, Department of Chemistry, University of Calgary, Calgary, Alberta T2N 1N4, Canada.
Alberta Glycomics Centre, Department of Chemistry, University of Calgary, Calgary, Alberta T2N 1N4, Canada.
Carbohydr Res. 2015 Jun 17;410:36-46. doi: 10.1016/j.carres.2015.04.003. Epub 2015 Apr 16.
An efficient O3-monodesilylation method has been developed for the derivatization of per-3-O-silylated cyclodextrin (CD) derivatives. Using hydrochloric acid as a reagent, the O3-monodesilylation was found to be regioselective, mild, practical and general as it can be applied to all α-, β- and γ-CDs. The advantage of the methodology is that the acid-catalyzed O3-desilylation can be carried out in a stepwise manner so that different types of functional groups can be introduced to a CD molecule at different stage of the O3-desilylations. This makes the current methodology flexible and versatile. This current methodology constitutes one of the few methodologies available for the regioselective modification of CDs at the secondary face.
已经开发出一种高效的O3-单去硅基化方法用于全-3-O-硅烷基化环糊精（CD）衍生物的衍生化。使用盐酸作为试剂，发现O3-单去硅基化具有区域选择性、温和、实用且通用，因为它可应用于所有α-、β-和γ-环糊精。该方法的优点是酸催化的O3-去硅基化可以逐步进行，从而可以在O3-去硅基化的不同阶段将不同类型的官能团引入到CD分子中。这使得当前方法灵活且通用。当前方法是可用于在二级面上对环糊精进行区域选择性修饰的少数方法之一。
