(1S,2R,3R,5S)-5-adenin-9-yl-3-benzyloxy-2-(hydroxymethyl)cyclohexanol | 205681-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (1S,2R,3R,5S)-5-adenin-9-yl-3-benzyloxy-2-(hydroxymethyl)cyclohexanol
• 英文别名: (1S,2R,3R,5S)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-3-phenylmethoxycyclohexan-1-ol
• CAS: 205681-12-5
• 化学式: C₁₉H₂₃N₅O₃
• 分子量: 369.423
• InChiKey: POZNYOVGLAFJIH-XUWVNRHRSA-N

物化性质

• 沸点：
  645.977±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.495±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R,5S)-5-adenin-9-yl-3-benzyloxy-2-(hydroxymethyl)cyclohexanol 在 palladium dihydroxide 环己烯 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以92%的产率得到5-(6-aminopurin-9-yl)-2-(hydroxymethyl)cyclohexane-1,3-diol
  参考文献：
  名称：

  Enantioselective Approach to the Synthesis of Cyclohexane Carbocyclic Nucleosides

  摘要：

  (R)-(-)-Carvone was used as starting material for the synthesis of a new series of 2-(hydroxymethyl)cyclohexane-1,3-diol nucleosides. The enantioselective precursors of the nucleoside analogues were obtained via a stereo-and regioselective hydroboration reaction. The compounds have equatorial oriented base moieties despite the presence of three other axial substituents.

  DOI：

  10.1021/jo972285c
• 作为产物：
  描述：

  (2R,5R,7R,9S,10S)-5-benzyloxy-2-phenylhexahydrobenzo[1.3]dioxin-7-ol 在 potassium carbonate 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 8.0h， 生成 (1S,2R,3R,5S)-5-adenin-9-yl-3-benzyloxy-2-(hydroxymethyl)cyclohexanol
  参考文献：
  名称：

  Enantioselective Approach to the Synthesis of Cyclohexane Carbocyclic Nucleosides

  摘要：

  (R)-(-)-Carvone was used as starting material for the synthesis of a new series of 2-(hydroxymethyl)cyclohexane-1,3-diol nucleosides. The enantioselective precursors of the nucleoside analogues were obtained via a stereo-and regioselective hydroboration reaction. The compounds have equatorial oriented base moieties despite the presence of three other axial substituents.

  DOI：

  10.1021/jo972285c

文献信息

• Enantioselective Approach to the Synthesis of Cyclohexane Carbocyclic Nucleosides
  作者：Jing Wang、Roger Busson、Norbert Blaton、Jef Rozenski、Piet Herdewijn

  DOI：10.1021/jo972285c

  日期：1998.5.1

  (R)-(-)-Carvone was used as starting material for the synthesis of a new series of 2-(hydroxymethyl)cyclohexane-1,3-diol nucleosides. The enantioselective precursors of the nucleoside analogues were obtained via a stereo-and regioselective hydroboration reaction. The compounds have equatorial oriented base moieties despite the presence of three other axial substituents.