Bhaumik Atanu, Samanta Supravat, Pathak Tanmaya
Department of Chemistry, Indian Institute of Technology Kharagpur , Kharagpur 721302, India.
J Org Chem. 2014 Aug 1;79(15):6895-904. doi: 10.1021/jo5009564. Epub 2014 Jul 10.
A wide range of stable vinyl selenone-modified furanosides has been synthesized for the first time. These 2π-partners undergo 1,3-dipolar cycloaddition reactions with a wide range of organic azides to afford enantiopure trisubstituted triazoles. Furanosyl rings opened up during triazole synthesis to generate polyfunctionalized molecules, ready to undergo further transformations. This strategy is one of the most convenient methods for the synthesis of enantiopure 1,4,5-trisubstituted 1,2,3-triazoles where the chiral components are attached to C-4 or C-5 position of triazole ring. These triazoles are formed in a regioselective manner, and several pairs of regioisomeric triazoles have also been synthesized. The approach affords densely functionalized triazoles, which are amenable to further modifications because of the presence of aldehyde and hydroxyl groups. This powerful and practical route adds to the arsenals of chemists and biologists interested in the synthesis and applications of triazoles.
首次合成了一系列稳定的乙烯基硒酮修饰的呋喃糖苷。这些2π反应物与多种有机叠氮化物发生1,3-偶极环加成反应，得到对映体纯的三取代三唑。呋喃糖环在三唑合成过程中打开，生成多官能化分子，可进一步进行转化。该策略是合成对映体纯的1,4,5-三取代1,2,3-三唑最简便的方法之一，其中手性组分连接在三唑环的C-4或C-5位。这些三唑以区域选择性方式形成，还合成了几对对映异构的三唑。该方法得到了密集官能化的三唑，由于存在醛基和羟基，易于进一步修饰。这条强大而实用的路线为对三唑合成和应用感兴趣的化学家和生物学家增添了新的手段。
