1-(5-O-tert-butyldimethylsilyl-3-deoxy-2-O-(phenoxy)-thionocarbonyl-3-C-trifluoromethyl-β-D-ribofuranosyl)-thymine | 219660-30-7

• 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: 1-(5-O-tert-butyldimethylsilyl-3-deoxy-2-O-(phenoxy)-thionocarbonyl-3-C-trifluoromethyl-β-D-ribofuranosyl)-thymine
• 英文别名: 1-[(2R,3R,4R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-phenoxycarbothioyloxy-4-(trifluoromethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 219660-30-7
• 化学式: C₂₄H₃₁F₃N₂O₆SSi
• 分子量: 560.667
• InChiKey: IMZLLSKPMLUIDF-SOAMZJECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(5-O-tert-butyldimethylsilyl-3-deoxy-2-O-(phenoxy)-thionocarbonyl-3-C-trifluoromethyl-β-D-ribofuranosyl)-thymine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以59%的产率得到1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-3-C-trifluoromethyl-β-D-erythropentofuranosyl)-thymine
  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：

  bis(trimethylsilyl)-2-thiothymine 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 Amberlite IRN-77 resin (H⁺) 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 40.0h， 生成 1-(5-O-tert-butyldimethylsilyl-3-deoxy-2-O-(phenoxy)-thionocarbonyl-3-C-trifluoromethyl-β-D-ribofuranosyl)-thymine
  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