1-(2',3',5'-tri-O-acetyl-4'-C-methyl-β-D-arabinofuranosyl)uracil | 175545-36-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2',3',5'-tri-O-acetyl-4'-C-methyl-β-D-arabinofuranosyl)uracil
• 英文别名: [(2R,3S,4S,5R)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)-2-methyloxolan-2-yl]methyl acetate
• CAS: 175545-36-5
• 化学式: C₁₆H₂₀N₂O₉
• 分子量: 384.343
• InChiKey: XCWQZNUUGXBLFG-TTZDDIAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(2',3',5'-tri-O-acetyl-4'-C-methyl-β-D-arabinofuranosyl)uracil 在 ammonium hydroxide 、 ClPhPOCl₂ 作用下， 以 吡啶 为溶剂， 生成 1-(4'-C-methyl-β-D-arabinofuranosyl)cytosine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 4′-C-Methyl Nucleosides

  摘要：

  A series of 2'-deoxy, 2',3'-unsaturated and 2',3'-dideoxynucleoside analogues, which have an additional methyl group at the 4'-position, have been synthesized. When evaluated for their inhibitory activity against HIV in MT-4 cell, 2'-deoxy-4'-C-methyl nucleosides exhibited potent activity.

  DOI：

  10.1080/07328319608002385
• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-4-bromo-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-methyl-tetrahydro-furan-3-yl ester 在 sodium hydroxide 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 、 苯 为溶剂， 反应 20.0h， 生成 1-(2',3',5'-tri-O-acetyl-4'-C-methyl-β-D-arabinofuranosyl)uracil
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 4′-C-Methyl Nucleosides

  摘要：

  A series of 2'-deoxy, 2',3'-unsaturated and 2',3'-dideoxynucleoside analogues, which have an additional methyl group at the 4'-position, have been synthesized. When evaluated for their inhibitory activity against HIV in MT-4 cell, 2'-deoxy-4'-C-methyl nucleosides exhibited potent activity.

  DOI：

  10.1080/07328319608002385