| 王永胜,赵玲,刘荣.化学通报,2020,83(1):88-91. |
| 一种非西他滨的合成方法 |
| A New Synthesis Method for Fiacitabine |
| 投稿时间：2019-08-02 修订日期：2019-10-12 |
| DOI： |
| 中文关键词: 非西他滨 苯甲酸酐 胞嘧啶 合成 |
| 英文关键词:Fiacitabine Benzoyl oxide Cytosine Synthesis |
| 基金项目:甘肃省属科研院所条件建设专项（18JR2TA002）资助 |
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| 中文摘要: |
| 非西他滨（Fiacitabine，FIAC）是一种嘧啶核苷类似物，具有抗各种疱疹病毒的活性。本文以2-脱氧-2-氟-三苯甲酰基-α-D-阿拉伯呋喃糖为原料，常温条件下，经过溴化氢醋酸溶液溴化得到2-脱氧-2-氟-三苯甲酰基-α-D-溴化阿拉伯呋喃糖（4）；再以胞嘧啶为原料经过碘化、Bz-保护得到N-（5-碘-2-氧代-1，2-二氢嘧啶-4-基）苯甲酰胺（5），最后中间体4和5反应后脱保护基得到非西他滨。整条路线反应原料廉价，反应步骤少，选择性高，总收率高达43%。 |
| 英文摘要: |
| Fiacitabine (FIAC) is a pyrimidine nucleoside analog with activity against various herpesviruses. In this paper, ((2R,3S,4S)-3-(benzoyloxy)-5-bromo-4-fluorotetrahydrofuran-2-yl)methyl benzoate (4) is afforded in high yields through brominiation, starting with (2R,3S,4R,5R)-5-(benzoyloxymethyl)-3-fluorotetrahydrofuran-2,4-dily dibenzoate at room temperature; and simultaneously N-(5-iodo-1,2-dihydropyrimidin-4-yl)benzamind (5) was effectively synthesized through two steps including iodobenzene, Bz-protection, starting with cytosine, which can be obtained cheaply and conveniently. Then FIAC is obtained by substitution reaction with intermediate 4 and 5 followed by deprotection reaction. This synthetic route has the advantages of brief reaction steps, convenient manipulation and high product selectivity for FIAC. The overall yield is 43%. |
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