5-O-acetyl-3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-α-D-ribofuranose | 219660-25-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-acetyl-3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-α-D-ribofuranose
• 英文别名: [(3aR,5S,6R,6aR)-2,2-dimethyl-6-(trifluoromethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl acetate
• CAS: 219660-25-0
• 化学式: C₁₁H₁₅F₃O₅
• 分子量: 284.232
• InChiKey: FSHASFYAZGKFLQ-FNCVBFRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-O-acetyl-3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-α-D-ribofuranose 在 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 吡啶 为溶剂， 反应 5.0h， 生成 1,2,5-tri-O-acetyl-3-deoxy-3-C-trifluoromethyl-β-D-ribofuranose
  参考文献：
  名称：

  3′-Deoxy-3′-C-trifluoromethyl Nucleosides: Synthesis and Antiviral Evaluation

  摘要：

  2',3'-Dideoxy-3'-C-trifluoromethylthymidine 9a and -uridine 9b and 3'-C-trifluoromethyl-d(4)T 11 were prepared in a few steps from 3'-deoxy-3'-C-trifluoromethyl-D-ribose, which synthesis was recently reported. The biological assessment of these nucleoside analogues did not reveal interesting antiviral properties against HIV-1, HSV-1, CMV, Vaccine, and Cox B4.

  DOI：

  10.1080/07328319808004316
• 作为产物：
  描述：

  乙酸酐 、 3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-α-D-ribofuranose 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以90%的产率得到5-O-acetyl-3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-α-D-ribofuranose
  参考文献：
  名称：

  3′-Deoxy-3′-C-trifluoromethyl Nucleosides: Synthesis and Antiviral Evaluation

  摘要：

  2',3'-Dideoxy-3'-C-trifluoromethylthymidine 9a and -uridine 9b and 3'-C-trifluoromethyl-d(4)T 11 were prepared in a few steps from 3'-deoxy-3'-C-trifluoromethyl-D-ribose, which synthesis was recently reported. The biological assessment of these nucleoside analogues did not reveal interesting antiviral properties against HIV-1, HSV-1, CMV, Vaccine, and Cox B4.

  DOI：

  10.1080/07328319808004316