1-(3-deoxy-3-trifluoromethyl-β-D-ribofuranosyl)thymine | 219660-28-3

• 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-(3-deoxy-3-trifluoromethyl-β-D-ribofuranosyl)thymine
• 英文别名: 1-(3-deoxy-3-C-trifluoromethyl-β-D-ribofuranosyl)-thymine；1-[(2R,3R,4S,5S)-3-hydroxy-5-(hydroxymethyl)-4-(trifluoromethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 219660-28-3
• 化学式: C₁₁H₁₃F₃N₂O₅
• 分子量: 310.23
• InChiKey: YKWMRAAXJUXCCN-JXOAFFINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(3-deoxy-3-trifluoromethyl-β-D-ribofuranosyl)thymine 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 19.0h， 生成 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 三氟甲磺酸三甲基硅酯 、 Amberlite IRN-77 resin (H⁺) 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 生成 1-(3-deoxy-3-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

文献信息

• Synthesis of 3′-Trifluoromethyl Nucleosides as Potential Antiviral Agents
  作者：Pawan K. Sharma、Vasu Nair

  DOI：10.1080/15257770008035023

  日期：2000.4

  1,2-Di-O-acetyl-3-deoxy-3-trifluoromethyl-5-O-benzoyl-beta-D-ribofuranos e was synthesized from the precursor keto sugar by the use of Ruppert's reagent (CF3SiMe3) as the source of a nucleophilic trifluoromethyl group. Coupling of this trifluoromethyl sugar with nucleobases and elaboration gave novel deoxy and dideoxynucleosides. A single crystal X-ray analysis confirmed the structure and stereochemistry

  使用Ruppert试剂（CF3SiMe3）作为前驱体酮糖，从前体酮糖合成1,2-二-O-乙酰基-3-脱氧-3-三氟甲基-5-O-苯甲酰基-β-D-核呋喃酮。亲核三氟甲基。将该三氟甲基糖与核碱基偶联并进行精制，得到了新颖的脱氧和双脱氧核苷。单晶X射线分析证实了结构和立体化学。通过消除反应将脱氧核苷转化为它们的双脱氧二氢衍生物。
• 3′-Deoxy-3′-<i>C</i>-trifluoromethyl Nucleosides: Synthesis and Antiviral Evaluation
  作者：S. Lavaire、R. Plantier-Royon、C. Portella、M. de Monte、A. Kirn、A.-M. Aubertin

  DOI：10.1080/07328319808004316

  日期：1998.12

  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.