(2R-cis)-4-(2-amino-9H-purin-9-yl)tetrahydro-2-furanmethanol | 141585-95-7

• 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: (2R-cis)-4-(2-amino-9H-purin-9-yl)tetrahydro-2-furanmethanol
• 英文别名: 4(S)-(2-amino-9H-purin-9-yl)tetrahydro-2(S)-furanmethanol；[(2S,4S)-4-(2-aminopurin-9-yl)oxolan-2-yl]methanol
• CAS: 141585-95-7
• 化学式: C₁₀H₁₃N₅O₂
• 分子量: 235.246
• InChiKey: PZGHCKPPIJNJSW-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氨基-6-氯嘌呤 在 palladium on activated charcoal 18-冠醚-6 、 氢气 、 sodium methylate 、 sodium acetate 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~70.0 ℃ 、275.79 kPa 条件下， 反应 2.0h， 生成 (2R-cis)-4-(2-amino-9H-purin-9-yl)tetrahydro-2-furanmethanol
  参考文献：
  名称：

  Synthesis and Conformational Studies of New Purine Isodideoxynucleosides

  摘要：

  The synthesis and NMR conformational correlations (preferred syn or anti) of new isomeric dideoxynucleosides of potential antiviral interest are described. These compounds are related to the potently active anti-HIV compound, (S,S)-isodideoxy-adenosine.

  DOI：

  10.1080/07328319608002371

文献信息

• Synthesis and anti-HIV activity of isonucleosides
  作者：Donna M. Huryn、Barbara C. Sluboski、Steve Y. Tam、Manfred Weigele、Iain Sim、Barry D. Anderson、Hiroaki Mitsuya、Samuel Broder

  DOI：10.1021/jm00091a001

  日期：1992.6

  A series of isomeric 2',3'-dideoxynucleosides which contains a modified carbohydrate moiety has been prepared. This class of compounds was designed to mimic the activity of known anti-HIV dideoxynucleosides, while imparting enhanced chemical and enzymatic stability. Isonucleosides containing the standard heterocyclic bases (A, C, G, T) were synthesized via nucleophilic addition of the base to an isomeric sugar unit. Modified derivatives were generated by manipulation of the intact isonucleoside. Two of the compounds prepared, iso-ddA (1) and iso-ddG (6), exhibit significant and selective anti-HIV activity, as well as beneficial hydrolytic stability.
• Synthesis and Conformational Studies of New Purine Isodideoxynucleosides
  作者：Lawrence B. Zintek、Tamera S. Jahnke、Vasu Nair

  DOI：10.1080/07328319608002371

  日期：1996.1

  The synthesis and NMR conformational correlations (preferred syn or anti) of new isomeric dideoxynucleosides of potential antiviral interest are described. These compounds are related to the potently active anti-HIV compound, (S,S)-isodideoxy-adenosine.