Dondoni Alessandro, Marra Alberto
Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, I-44100 Ferrara, Italy.
J Org Chem. 2006 Sep 29;71(20):7546-57. doi: 10.1021/jo0607156.
A route has been paved toward the preparation of triazole glycocluster libraries via the copper(I)-catalyzed modern version of the classical Huisgen 1,3-dipolar cycloaddition of azides to alkynes. Up to four 1,4-disubstituted 1,2,3-triazole rings bearing carbon-linked glycosyl fragments were constructed on various scaffolds via multiple cycloadditions of suitably polyfunctionalized calix[4]arene, adamantane, and benzene derivatives with ethynyl and azidomethyl C-glycosides. Each cycloaddition occurred with high regioselectivity to give exclusively the 1,4-disubstituted triazole ring in very high yield up to an average value of 98%. The high degree of efficiency of this approach and its wide scope constitute a simple and practical means for the attachment of various sugar units to polyfunctionalized substrates.
通过铜（I）催化的经典惠斯根叠氮化物与炔烃的1,3-偶极环加成反应的现代版本，已为制备三唑糖簇文库铺平了道路。通过将适当多官能化的杯[4]芳烃、金刚烷和苯衍生物与乙炔基和叠氮甲基C-糖苷进行多次环加成反应，在各种支架上构建了多达四个带有碳连接糖基片段的1,4-二取代1,2,3-三唑环。每次环加成反应都具有很高的区域选择性，以非常高的产率（平均高达98%）专一性地生成1,4-二取代的三唑环。这种方法的高度效率及其广泛的适用范围构成了一种将各种糖单元连接到多官能化底物上的简单实用方法。
