9-[[(1R,2S,3S)-2,3-bis(phenylmethoxymethyl)cyclopentyl]methyl]purin-6-amine | 256221-98-4

• 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-[[(1R,2S,3S)-2,3-bis(phenylmethoxymethyl)cyclopentyl]methyl]purin-6-amine
• CAS: 256221-98-4
• 化学式: C₂₇H₃₁N₅O₂
• 分子量: 457.575
• InChiKey: BWYIXGGBKOMJEU-VXNXHJTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  88.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-[[(1R,2S,3S)-2,3-bis(phenylmethoxymethyl)cyclopentyl]methyl]purin-6-amine 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到[(1S,2S,3R)-3-[(6-aminopurin-9-yl)methyl]-2-(hydroxymethyl)cyclopentyl]methanol
  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：

  京尼平甙 在 palladium on activated charcoal 盐酸 、 氢气 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 臭氧 、 copper(II) sulfate 、 高碘酸 、 三乙胺 、 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 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 113.25h， 生成 9-[[(1R,2S,3S)-2,3-bis(phenylmethoxymethyl)cyclopentyl]methyl]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+

文献信息

• Stereoselective Hydrogenation and Ozonolysis of Iridoids. Conversion into Carbocyclic Nucleoside Analogues
  作者：Henrik Franzyk、Frank R. Stermitz

  DOI：10.1021/np990288+

  日期：1999.12.1

  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).