[(1S,2R,3S)-2-(benzoyloxymethyl)-3-[(1S)-1,2-dihydroxyethyl]cyclopentyl]methyl benzoate | 256221-95-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1S,2R,3S)-2-(benzoyloxymethyl)-3-[(1S)-1,2-dihydroxyethyl]cyclopentyl]methyl benzoate
• CAS: 256221-95-1
• 化学式: C₂₃H₂₆O₆
• 分子量: 398.456
• InChiKey: JXMQDHIKNPYOGG-PLACYPQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1S,2R,3S)-2-(benzoyloxymethyl)-3-[(1S)-1,2-dihydroxyethyl]cyclopentyl]methyl benzoate 在 sodium tetrahydroborate 、 氨 、 高碘酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 84.5h， 生成 [(1S,2S,3S)-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 吡啶 、 盐酸 、 氢气 、 4-甲基苯磺酸吡啶 、 臭氧 、 copper(II) sulfate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 84.0h， 生成 [(1S,2R,3S)-2-(benzoyloxymethyl)-3-[(1S)-1,2-dihydroxyethyl]cyclopentyl]methyl benzoate
  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+