4',6'-O-isopropylidene-aucubin | 256221-84-8

• 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: 4',6'-O-isopropylidene-aucubin
• 英文别名: (4aR,6S,7R,8R,8aS)-6-[[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 256221-84-8
• 化学式: C₁₈H₂₆O₉
• 分子量: 386.399
• InChiKey: IOSZYANINMRPTQ-SKYGNZQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4',6'-O-isopropylidene-aucubin 在 铂 三乙胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 10α-4',6'-O-isopropylidene-3,4,7,8-tetrahydroaucubin 、 10β-4',6'-O-isopropylidene-3,4,7,8-tetrahydroaucubin
  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：

  isoscrophularioside 在 sodium hydroxide 、 4-甲基苯磺酸吡啶 、 copper(II) sulfate 作用下， 以 丙酮 为溶剂， 反应 98.0h， 生成 4',6'-O-isopropylidene-aucubin
  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).