[(1S,2R,3S)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(hydroxymethyl)cyclopentyl]methanol | 256221-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1S,2R,3S)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(hydroxymethyl)cyclopentyl]methanol
• CAS: 256221-91-7
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: CZGYYYXETZVGBD-LMLFDSFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1S,2R,3S)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(hydroxymethyl)cyclopentyl]methanol 在 盐酸 、 sodium hydride 、 高碘酸 作用下， 以 四氢呋喃 为溶剂， 反应 24.25h， 生成 [(1S,2S,3S)-2,3-bis(phenylmethoxymethyl)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：

  4',6'-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide 在 sodium tetrahydroborate 、 4-甲基苯磺酸吡啶 、 copper(II) sulfate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 8.5h， 生成 [(1S,2R,3S)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-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+