3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-α-D-ribofuranose | 177361-84-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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]methanol
• CAS: 177361-84-1
• 化学式: C₉H₁₃F₃O₄
• 分子量: 242.195
• InChiKey: RXWPYCSZYFKLTD-DBRKOABJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-α-D-ribofuranose 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 Amberlite IRN-77 resin (H⁺) 、 三正丁基氢锡 、 sodium methylate 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 66.0h， 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：

  (R)-1-((3aR,5S,6aR)-2,2-Dimethyl-6-trifluoromethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethane-1,2-diol 在 sodium tetrahydroborate 、 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 反应 3.5h， 生成 3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis of 3-Deoxy-3-C-Trifluoromethyl-d-Ribose Fromd-Xylose ord-Glucose

  摘要：

  The synthesis of 3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-alpha-D-ribofuranose is described. After a first approach from a commercial D-xylose derivative which was limited by an incomplete stereoselectivity, the synthesis of the title compound was performed from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose by a reaction sequence where key steps: trifluoromethylation with CF(3)SiMe(3) and radical deoxygenation are highly stereoselective.

  DOI：

  10.1080/07328309608005659

文献信息

• Synthesis of 3-Deoxy-3-<i>C</i>-Trifluoromethyl-<scp>d</scp>-Ribose From<scp>d</scp>-Xylose or<scp>d</scp>-Glucose
  作者：S. Lavaire、R. Plantier-Royon、C. Portella

  DOI：10.1080/07328309608005659

  日期：1996.4

  The synthesis of 3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-alpha-D-ribofuranose is described. After a first approach from a commercial D-xylose derivative which was limited by an incomplete stereoselectivity, the synthesis of the title compound was performed from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose by a reaction sequence where key steps: trifluoromethylation with CF(3)SiMe(3) and radical deoxygenation are highly stereoselective.
• 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.