(1R,2R,3S,5S)-3-methoxymethoxy-2-benzyloxymethyl-6-oxabicyclo[3.1.0]hexane | 848750-01-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R,3S,5S)-3-methoxymethoxy-2-benzyloxymethyl-6-oxabicyclo[3.1.0]hexane
• 英文别名: (1R,2R,3S,5S)-3-(methoxymethoxy)-2-(phenylmethoxymethyl)-6-oxabicyclo[3.1.0]hexane
• CAS: 848750-01-6
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: GDRPJGTYSZKTQH-CBBWQLFWSA-N

物化性质

• 沸点：
  348.9±37.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,5S)-3-methoxymethoxy-2-benzyloxymethyl-6-oxabicyclo[3.1.0]hexane 在 15-冠醚-5 、 三氯化硼 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 (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,5S)-5-Methoxymethoxy-cyclopent-2-enyl)-methanol 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (1R,2R,3S,5S)-3-methoxymethoxy-2-benzyloxymethyl-6-oxabicyclo[3.1.0]hexane
  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

文献信息

• 5′-Noraristeromycin derivatives isomeric to aristeromycin and 2′-deoxyaristeromycin
  作者：Xue-qiang Yin、Stewart W. Schneller

  DOI：10.1016/j.tet.2004.12.016

  日期：2005.2

  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.