A new concept for the preparation of β-L- and β-D-2′,3-dideoxynucleoside analogues
A new concept for the preparation of β-L- and β-D-2′,3-dideoxynucleoside analogues
复制标题
DOI：
10.1021/ol026460
复制
发表时间：
2002-09-19
期刊：
影响因子：
5.2
通讯作者：
Hönig, H
中科院分区：
文献类型：
--
作者：
Albert, M;De Souza, D;Hönig, H
发展了一种合成2 ′，3 ′-双脱氧核苷类似物的新方法。2-取代的呋喃的电化学活化之后是与嘧啶或嘌呤碱的偶联。这得到作为关键中间体的呋喃基核苷，其顺式选择性氢化以得到作为外消旋混合物的相应β-2 '，3'-二脱氧核苷。酶动力学拆分产生高光学纯度的β-D-和β-L-构型衍生物。这通过β-D-和β-L-3 '-脱氧胸苷的合成来举例说明。
A new method for the synthesis of 2',3'-dideoxynucleoside analogues has been developed. An electrochemical activation of 2-substituted furans is followed by the coupling with a pyrimidine or purine base. This gives furyl nucleosides as key intermediates, which are hydrogenated cis-selectively to give the corresponding beta-2',3'-dideoxynucleosides as racemic mixtures. An enzymatic kinetic resolution gives rise to beta-D- and beta-L-configured derivatives in high optical purity. This is exemplified by the synthesis of beta-D- and beta-L-3'-deoxythymidine.