Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Via P. Giuria 9, 10125 Torino, Italy.
Carbohydr Res. 2011 Dec 13;346(17):2677-82. doi: 10.1016/j.carres.2011.09.018. Epub 2011 Sep 22.
New highly soluble β-aminoalcohol β-cyclodextrin (β-CD) derivatives have been synthesized via nucleophilic epoxide opening reactions with mono-6-amino mono-6-deoxy-permethyl-β-CD and mono-6-amino mono-6-deoxy-β-CD. The binding properties of the β-CD were enhanced by linking aminoalcohol subunits which caused its solubility to improve markedly. The reaction conditions were optimised using microwave irradiation giving moderate-to-good yields with a series of epoxides. A regioselective epoxide opening reaction was observed in the reaction with styrene oxide while the stereoselectivity was strictly dependent on substrate structure.
新型高水溶性β-氨基醇β-环糊精（β-CD）衍生物通过亲核环氧化物开环反应与单-6-氨基单-6-去氧-全甲基-β-CD 和单-6-氨基单-6-去氧-β-CD 合成。通过连接氨基醇亚基增强了β-CD 的结合性能，导致其溶解度显著提高。使用微波辐射优化了反应条件，对一系列环氧化物的产率适中至良好。在与氧化苯乙烯的反应中观察到区域选择性开环反应，而立体选择性严格取决于底物结构。
