(2S,3S,4R,5S)-2-((benzoyloxy)methyl)-5-(2,4-dioxo-5-(thiophen-2-yl)-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate | 1382804-41-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: (2S,3S,4R,5S)-2-((benzoyloxy)methyl)-5-(2,4-dioxo-5-(thiophen-2-yl)-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate
• CAS: 1382804-41-2
• 化学式: C₃₄H₂₆N₂O₉S
• 分子量: 638.654
• InChiKey: NWXCJQLQDMAHFZ-HRLCWXNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  46.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  142.99
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S)-2-((benzoyloxy)methyl)-5-(2,4-dioxo-5-(thiophen-2-yl)-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate 在 N-碘代丁二酰亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以97%的产率得到(2S,3S,4R,5S)-2-((benzoyloxy)methyl)-5-(5-(5-iodothiophen-2-yl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Synthesis and Cytotoxic Activity of Novel 5-Substituted-1-(β-L-Arabinofuranosyl) Pyrimidine Nucleosides

  摘要：

  A series of new 5-halogeno-1-(beta-L-arabinofuranosyl)uracils and their cytosine analogues were synthesized by halogenation of ara-L-uridine and ara-L-cytidine, respectively. The 5-(2-thienyl) and 5-halogenothienyl derivatives of both series were also prepared in excellent yields by Stille coupling followed by halogenation. All of these syntheses were based on benzoyl-protected derivatives. In vitro cytotoxicity experiments carried out using L1210 mouse leukemia cells showed that 5-(2-thienyl)-ara-L-uridine was the most potent compound of the new compounds; the majority of the analogues were not effective up to 200 mu M concentrations.

  DOI：

  10.1080/15257770.2012.689410
• 作为产物：
  描述：

  1-(β-L-arabinofuranosyl)uracil 在 吡啶 、 N-碘代丁二酰亚胺 、 四(三苯基膦)钯 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.25h， 生成 (2S,3S,4R,5S)-2-((benzoyloxy)methyl)-5-(2,4-dioxo-5-(thiophen-2-yl)-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Synthesis and Cytotoxic Activity of Novel 5-Substituted-1-(β-L-Arabinofuranosyl) Pyrimidine Nucleosides

  摘要：

  A series of new 5-halogeno-1-(beta-L-arabinofuranosyl)uracils and their cytosine analogues were synthesized by halogenation of ara-L-uridine and ara-L-cytidine, respectively. The 5-(2-thienyl) and 5-halogenothienyl derivatives of both series were also prepared in excellent yields by Stille coupling followed by halogenation. All of these syntheses were based on benzoyl-protected derivatives. In vitro cytotoxicity experiments carried out using L1210 mouse leukemia cells showed that 5-(2-thienyl)-ara-L-uridine was the most potent compound of the new compounds; the majority of the analogues were not effective up to 200 mu M concentrations.

  DOI：

  10.1080/15257770.2012.689410