2,2,2-Trifluoro-N-{8-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxymethoxy]-octyl}-acetamide | 155195-47-4

• 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: 2,2,2-Trifluoro-N-{8-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxymethoxy]-octyl}-acetamide
• 英文别名: 2,2,2-trifluoro-N-[8-[[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxymethoxy]octyl]acetamide
• CAS: 155195-47-4
• 化学式: C₂₁H₃₂F₃N₃O₇
• 分子量: 495.496
• InChiKey: ONGOHSABNZJVGT-GVDBMIGSSA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,2,2-Trifluoro-N-{8-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxymethoxy]-octyl}-acetamide 在 1H-1,2,3-三氮唑 、 ammonium hydroxide 、 bis(butylammonium)pyrophosphate 、 三乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of 3′-O-(ω-aminoalkoxymethyl)thymidine 5′-triphosphates, terminators of DNA synthesis that enable 3′-labelling

  摘要：

  Treatment of 5'-O-benzoylthymidine 1 with a mixture of acetic anhydride. acetic acid and dimethyl sulfoxide yielded 5'-O-benzoyl-3'-O-methylthiomethylthymidine 2, which was converted via the 3'-O-bromomethyl derivative into 3'-O-(omega-aminoalkoxymethyl)thymidines 7 bearing a 6, 8 or 10 methylene groups long hydrocarbon chain, and finally to their 5'-triphosphates 10. The latter compounds were shown to be terminators of DNA synthesis catalysed by thermostable Tet/z DNA-polymerase, and may be labelled at the aliphatic amino group with fluorescent probes.

  DOI：

  10.1039/p19940000211
• 作为产物：
  描述：

  8-溴-1-辛醇 在 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 lutidine 、 氨 、 氯化铵 、 三苯基膦 、 lithium chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 2,2,2-Trifluoro-N-{8-[(2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxymethoxy]-octyl}-acetamide
  参考文献：
  名称：

  Synthesis of 3′-O-(ω-aminoalkoxymethyl)thymidine 5′-triphosphates, terminators of DNA synthesis that enable 3′-labelling

  摘要：

  Treatment of 5'-O-benzoylthymidine 1 with a mixture of acetic anhydride. acetic acid and dimethyl sulfoxide yielded 5'-O-benzoyl-3'-O-methylthiomethylthymidine 2, which was converted via the 3'-O-bromomethyl derivative into 3'-O-(omega-aminoalkoxymethyl)thymidines 7 bearing a 6, 8 or 10 methylene groups long hydrocarbon chain, and finally to their 5'-triphosphates 10. The latter compounds were shown to be terminators of DNA synthesis catalysed by thermostable Tet/z DNA-polymerase, and may be labelled at the aliphatic amino group with fluorescent probes.

  DOI：

  10.1039/p19940000211