1-(2-Deoxy-β-D-erythro-pentofuranosyl)-4-(pentafluorophenyloxy)-2(1H)-pyrimidinone | 170114-35-9

• 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-(2-Deoxy-β-D-erythro-pentofuranosyl)-4-(pentafluorophenyloxy)-2(1H)-pyrimidinone
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(2,3,4,5,6-pentafluorophenoxy)pyrimidin-2-one；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(2,3,4,5,6-pentafluorophenoxy)pyrimidin-2-one
• CAS: 170114-35-9
• 化学式: C₁₅H₁₁F₅N₂O₅
• 分子量: 394.255
• InChiKey: NSRDUYPRJLONEY-SHYZEUOFSA-N

物化性质

• 沸点：
  500.3±60.0 °C(predicted)
• 密度：
  1.76±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[3-[3-aminopropyl-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]amino]propyl]carbamate 、 1-(2-Deoxy-β-D-erythro-pentofuranosyl)-4-(pentafluorophenyloxy)-2(1H)-pyrimidinone 以 1,4-二氧六环 为溶剂， 以58%的产率得到tert-butyl N-[3-[3-[[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]amino]propyl-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]amino]propyl]carbamate
  参考文献：
  名称：

  1-（2'-脱氧β - D-赤型-戊呋喃糖基）-4-五氟苯基嘧啶-2 H -one的直接合成，取代和结构

  摘要：

  已经开发了直接方法以从2'-脱氧尿苷（dU）访问标题核苷1。的C-4五氟苯基1可容易地通过形成良好N-4取代的胞嘧啶到优异的产率胺亲核试剂置换。

  DOI：

  10.1016/0040-4039(95)00587-3
• 作为产物：
  描述：

  在 吡啶 、 silica gel 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 1-(2-Deoxy-β-D-erythro-pentofuranosyl)-4-(pentafluorophenyloxy)-2(1H)-pyrimidinone
  参考文献：
  名称：

  Synthesis and anti-HIV activity of C4-modified pyrimidine nucleosides

  摘要：

  One-pot syntheses provided a series of triazole- and pentafluorophenyloxy-substituted pyrimidine nucleosides. Most of the compounds in the series displayed anti-HIV activities but none as potent as AZT 2. 1-(beta-D-Erythro-pentofuranosyl)-4-pentafluorophenyloxy-2(1H)-pyr imidinone 14 was the most potent and the most selective compound in the series with EC50 = 1.6 microM.

  DOI：

  10.1016/s0014-827x(98)00107-4

文献信息

• Direct synthesis, substitution, and structure of 1-(2′-deoxyβ-D-erythro-pentofuranosyl)-4-pentafluorophenylpyrimidin-2H-one
  作者：Mark P. Wallis、Ian D. Spiers、Carl H. Schwalbe、William Fraser

  DOI：10.1016/0040-4039(95)00587-3

  日期：1995.5

  Direct methods have been developed to access the title nucleoside 1 from 2′-deoxyuridine (dU). The C-4 pentafluorophenyl group of 1 is readily displaced by amine nucleophiles forming N-4 substituted cytosines in good to excellent yields.

  已经开发了直接方法以从2'-脱氧尿苷（dU）访问标题核苷1。的C-4五氟苯基1可容易地通过形成良好N-4取代的胞嘧啶到优异的产率胺亲核试剂置换。
• Synthesis and anti-HIV activity of C4-modified pyrimidine nucleosides
  作者：Mark P Wallis、Naheed Mahmood、William Fraser

  DOI：10.1016/s0014-827x(98)00107-4

  日期：1999.1

  One-pot syntheses provided a series of triazole- and pentafluorophenyloxy-substituted pyrimidine nucleosides. Most of the compounds in the series displayed anti-HIV activities but none as potent as AZT 2. 1-(beta-D-Erythro-pentofuranosyl)-4-pentafluorophenyloxy-2(1H)-pyr imidinone 14 was the most potent and the most selective compound in the series with EC50 = 1.6 microM.