Synthesis of the First Selenium-Containing Acyclic Nucleosides and Anomeric Spironucleosides from Carbohydrate Precursors
作者:Susana Maza、Óscar López、Sergio Martos、Inés Maya、José G. Fernández-Bolaños
DOI:10.1002/ejoc.200900793
日期:2009.10
We report the synthesis of acyclic and spiranic imidazole-derived C-selenonucleosides. 5-Hydroxy-4-tetrahydroxybutyl imidazolidine-2-selones, a novel class of acyclic selenonucleosides, were transformed into (tetrahydroxybutylimidazol-2-yl)diselenide, by acetylation and chemoselective N-deacetylation with methanolic imidazole. Furthermore, the synthesis of a new class of conformationally restricted
我们报告了无环和螺旋咪唑衍生的 C-硒代核苷的合成。5-Hydroxy-4-tetrahydroxybutyl imidazolide-2-selones 是一类新型的无环硒核苷,通过乙酰化和化学选择性 N-脱乙酰作用与甲醇咪唑转化为(四羟基丁基咪唑-2-基)二硒化物。此外,从 N-果糖胺开始,通过 4-羟基-4-四羟丁基-咪唑烷-2-selones 合成了一类新的构象受限的阿拉伯结构螺核苷,该螺核苷在糖苷键周围含有一个咪唑烷-2-selone 单元作为关键中间体。这些中间体的乙酰化-脱乙酰化得到稳定的芳香族咪唑啉-2-selones。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)