(1R,2S,3S,5R)-5-(6-aminopurin-9-yl)-2-benzyloxymethyl-3-(methoxymethoxy)cyclopentanol | 848750-03-8

• 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: (1R,2S,3S,5R)-5-(6-aminopurin-9-yl)-2-benzyloxymethyl-3-(methoxymethoxy)cyclopentanol
• 英文别名: (1R,2S,3S,5R)-5-(6-aminopurin-9-yl)-3-(methoxymethoxy)-2-(phenylmethoxymethyl)cyclopentan-1-ol
• CAS: 848750-03-8
• 化学式: C₂₀H₂₅N₅O₄
• 分子量: 399.45
• InChiKey: SNISEDSOKPMCNG-XLMAVXFVSA-N

物化性质

• 沸点：
  614.5±65.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,5R)-5-(6-aminopurin-9-yl)-2-benzyloxymethyl-3-(methoxymethoxy)cyclopentanol 在 三氯化硼 、 甲醇 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以10%的产率得到(1S,2R,3R,4R)-4-(6-aminopurin-9-yl)-2-(hydroxymethyl)cyclopentane-1,3-diol
  参考文献：
  名称：

  5′-Noraristeromycin derivatives isomeric to aristeromycin and 2′-deoxyaristeromycin

  摘要：

  A straightforward synthesis of (1S,2R,3R,4R)-4-(6-aminopurin-9-yl)-2-hydroxymethylcyclopentane-1,3-diol (2), an isomer of aristeromycin, and its 2'-deoxy derivative 3 from readily available disubstituted cyclopentenes is presented. An antiviral analysis of 2 showed it to have significant activity versus Epstein-Barr virus (IC50 0.62 mug/mL in the Elisa assay) and to be free of cytotoxicity effects against the host cells. In a much less comprehensive antiviral analysis, 3 also was active towards Epstein-Barr (IC50 7.58 mug/mL in the Elisa assay) but this was accompanied by cellular toxicity. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.016
• 作为产物：
  描述：

  ((1R,2R,3S,5S)-3-Methoxymethoxy-6-oxa-bicyclo[3.1.0]hex-2-yl)-methanol 在 15-冠醚-5 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 (1R,2S,3S,5R)-5-(6-aminopurin-9-yl)-2-benzyloxymethyl-3-(methoxymethoxy)cyclopentanol
  参考文献：
  名称：

  5′-Noraristeromycin derivatives isomeric to aristeromycin and 2′-deoxyaristeromycin

  摘要：

  A straightforward synthesis of (1S,2R,3R,4R)-4-(6-aminopurin-9-yl)-2-hydroxymethylcyclopentane-1,3-diol (2), an isomer of aristeromycin, and its 2'-deoxy derivative 3 from readily available disubstituted cyclopentenes is presented. An antiviral analysis of 2 showed it to have significant activity versus Epstein-Barr virus (IC50 0.62 mug/mL in the Elisa assay) and to be free of cytotoxicity effects against the host cells. In a much less comprehensive antiviral analysis, 3 also was active towards Epstein-Barr (IC50 7.58 mug/mL in the Elisa assay) but this was accompanied by cellular toxicity. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.016