Design and synthesis of a novel ring-expanded 4′-thio-apio-nucleoside derivatives
Design and synthesis of a novel ring-expanded 4′-thio-apio-nucleoside derivatives
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DOI：
10.1016/j.tetlet.2007.04.139
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发表时间：
2007-06-25
影响因子：
1.8
通讯作者：
Takahata, Hiroki
中科院分区：
文献类型：
--
作者：
Yoshimura, Yuichi;Yamazaki, Yoshiko;Takahata, Hiroki
本文报道了一种具有抗HIV活性的扩环4 ′-硫代-阿朴-核苷衍生物4的合成。由2-丁烯-1，4-二醇制备的环氧醇衍生物10经3步转化为烯丙基硫醚衍生物13。13的闭环复分解得到二氢噻喃衍生物20，其进一步转化为亚砜24。将24与过甲硅烷基化尿嘧啶衍生物进行Pummerer型巯基糖基化反应，然后转化为胞嘧啶衍生物并脱保护，以良好的产率得到扩环的4 ′-硫代-apio-核苷衍生物4的外消旋混合物。(c)2007爱思唯尔有限公司保留所有权利。
The synthesis of a ring-expanded 4'-thio-apio-nucleoside derivative 4, designed to serve as a potential anti-HIV agent, is described. The epoxy alcohol derivative 10, prepared from 2-butene-1,4-diol, was converted to an allylsulfide derivative 13 in 3 steps. Ring-closing-metathesis of 13 gave the dihydrothiopyran derivative 20, which was further converted into sulphoxide 24. A Pummerer-type thioglycosylation reaction of 24 with a persilylated uracil derivative, followed by conversion to a cytosine derivative and deprotection, gave a racemic mixture of the ring-expanded 4'-thio-apio-nucleoside derivative 4 in good yield. (c) 2007 Elsevier Ltd. All rights reserved.