9,9'-(((1S,2R,3S)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclopentane-1,2-diyl)bis(methylene))bis(9H-purin-6-amine) | 256221-99-5

• 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: 9,9'-(((1S,2R,3S)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclopentane-1,2-diyl)bis(methylene))bis(9H-purin-6-amine)
• CAS: 256221-99-5
• 化学式: C₂₂H₂₈N₁₀O₂
• 分子量: 464.53
• InChiKey: PVGHKPIISBHRPZ-LXTVHRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  157.7
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  9,9'-(((1S,2R,3S)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclopentane-1,2-diyl)bis(methylene))bis(9H-purin-6-amine) 在 盐酸 作用下， 反应 36.0h， 以94 mg的产率得到(1S)-1-[(1S,2R,3S)-2,3-bis[(6-aminopurin-9-yl)methyl]cyclopentyl]ethane-1,2-diol
  参考文献：
  名称：

  Stereoselective Hydrogenation and Ozonolysis of Iridoids. Conversion into Carbocyclic Nucleoside Analogues

  摘要：

  Stereoselective hydrogenation of the iridoids geniposide (9) and aucubin (19) was achieved by using the 1-methyl-1-methoxyethyl ether as a protecting group for the allylic alcohol, as it enhanced the stereoselectivity and prevented undesired hydrogenolysis. Ozonolysis of the hydrogenation product from 9, adoxoside (11), with reductive workup, afforded either a chiral lactone (25) or a chiral polyol (26), depending on the reduction conditions. Polyol 26 was subjected to protecting-group manipulation and subsequent oxidation and reductions to yield cyclopentane building blocks (29-34), which, by Mitsunobu couplings with purines, afforded carbocyclic nucleoside analogues (7, 8, and 35).

  DOI：

  10.1021/np990288+
• 作为产物：
  描述：

  [(1S,2R,3S)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(hydroxymethyl)cyclopentyl]methanol 在 氨 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 9,9'-(((1S,2R,3S)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclopentane-1,2-diyl)bis(methylene))bis(9H-purin-6-amine)
  参考文献：
  名称：

  Stereoselective Hydrogenation and Ozonolysis of Iridoids. Conversion into Carbocyclic Nucleoside Analogues

  摘要：

  Stereoselective hydrogenation of the iridoids geniposide (9) and aucubin (19) was achieved by using the 1-methyl-1-methoxyethyl ether as a protecting group for the allylic alcohol, as it enhanced the stereoselectivity and prevented undesired hydrogenolysis. Ozonolysis of the hydrogenation product from 9, adoxoside (11), with reductive workup, afforded either a chiral lactone (25) or a chiral polyol (26), depending on the reduction conditions. Polyol 26 was subjected to protecting-group manipulation and subsequent oxidation and reductions to yield cyclopentane building blocks (29-34), which, by Mitsunobu couplings with purines, afforded carbocyclic nucleoside analogues (7, 8, and 35).

  DOI：

  10.1021/np990288+