N-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-2-oxo-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)pyrimidin-4-yl]benzamide | 1350820-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-2-oxo-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)pyrimidin-4-yl]benzamide
• CAS: 1350820-78-8
• 化学式: C₅₄H₅₅F₁₃N₅O₈P
• 分子量: 1180.01
• InChiKey: RIVNAIUXQIDDDB-GFNFZXEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  81
• 可旋转键数：
  26
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  23

反应信息

• 作为产物：
  描述：

  5-碘-2'-脱氧胞苷 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 三氟甲苯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.83h， 生成 N-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-2-oxo-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)pyrimidin-4-yl]benzamide
  参考文献：
  名称：

  Design, Synthesis, and Incorporation of Fluorous 5-Methylcytosines into Oligonucleotides

  摘要：

  A palladium-catalyzed Negishi coupling reaction has been developed to synthesize fluorous 5-methylcytosines. These fluorous nucleosides are incorporated into the oligonucleotides that correspond to part of the promoter region of Oct4, a master gene that undergoes dynamic DNA demethylation during cellular reprogramming. The separation of the fluorous oligonucleotides from its nonfluorous analogues has been achieved through solid-phase extraction over fluorous silica, suggesting its potential use in probing DNA demethylation.

  DOI：

  10.1021/jo2015399

文献信息

• Design, Synthesis, and Incorporation of Fluorous 5-Methylcytosines into Oligonucleotides
  作者：Zhiquan Song、Qisheng Zhang

  DOI：10.1021/jo2015399

  日期：2011.12.16

  A palladium-catalyzed Negishi coupling reaction has been developed to synthesize fluorous 5-methylcytosines. These fluorous nucleosides are incorporated into the oligonucleotides that correspond to part of the promoter region of Oct4, a master gene that undergoes dynamic DNA demethylation during cellular reprogramming. The separation of the fluorous oligonucleotides from its nonfluorous analogues has been achieved through solid-phase extraction over fluorous silica, suggesting its potential use in probing DNA demethylation.