Acetic acid (2R,3R,4S,5S)-2-acetoxymethyl-4-bromo-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester | 181025-79-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: Acetic acid (2R,3R,4S,5S)-2-acetoxymethyl-4-bromo-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3R,4S,5S)-3-acetyloxy-4-bromo-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 181025-79-6
• 化学式: C₁₃H₁₅BrN₂O₇
• 分子量: 391.175
• InChiKey: GIERFVXRTOJITJ-KLHWPWHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5S)-2-acetoxymethyl-4-bromo-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 在 三正丁基氢锡 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 生成 Acetic acid (2R,3S,5S)-2-acetoxymethyl-5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis and ribonuclease H related biochemical properties of α-anomeric 2′-deoxypyrimidine homooligomer and its phosphorothioate analog

  摘要：

  RNase H mediated degradation of RNA on the beta-DNA . RNA duplex was inhibited by the presence of extra 2'-deoxypyrimidine homooligomer. The effect was dependent on the nature of the nucleobase, glycoside bond configuration, and the internucleotide linkage of the extra homooligomer used. Thus, alpha-anomeric 2'-deoxycytidylate phosphorothioate exhibited the most potent inhibitory effect (> 40%) on RNase H. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00328-9
• 作为产物：
  描述：

  2,2'-anhydro-α-uridine 、 乙酰溴 生成 Acetic acid (2R,3R,4S,5S)-2-acetoxymethyl-4-bromo-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis and ribonuclease H related biochemical properties of α-anomeric 2′-deoxypyrimidine homooligomer and its phosphorothioate analog

  摘要：

  RNase H mediated degradation of RNA on the beta-DNA . RNA duplex was inhibited by the presence of extra 2'-deoxypyrimidine homooligomer. The effect was dependent on the nature of the nucleobase, glycoside bond configuration, and the internucleotide linkage of the extra homooligomer used. Thus, alpha-anomeric 2'-deoxycytidylate phosphorothioate exhibited the most potent inhibitory effect (> 40%) on RNase H. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00328-9