(4S,4aS,7S,7aR)-4-hydroxy-7-(hydroxymethyl)-4,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyran-3-one | 256221-89-3

• 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: (4S,4aS,7S,7aR)-4-hydroxy-7-(hydroxymethyl)-4,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyran-3-one
• CAS: 256221-89-3
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: BKMKPQWBCVWFAB-CWKFCGSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,4aS,7S,7aR)-4-hydroxy-7-(hydroxymethyl)-4,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyran-3-one 在 sodium tetrahydroborate 、 氨 、 4-甲基苯磺酸吡啶 、 copper(II) sulfate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 80.5h， 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+
• 作为产物：
  描述：

  京尼平甙 在 4-甲基苯磺酸吡啶 作用下， 以 丙酮 为溶剂， 反应 36.0h， 生成 (4S,4aS,7S,7aR)-4-hydroxy-7-(hydroxymethyl)-4,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyran-3-one
  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).