(1S,2S,3R,5S,8R,9R,10R,13S)-8,12,15,15-Tetramethyl-4-methylene-tricyclo[9.3.1.0^3,8]pentadec-11-ene-1,2,5,9,10,13-hexaol | 138613-22-6

• 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,2S,3R,5S,8R,9R,10R,13S)-8,12,15,15-Tetramethyl-4-methylene-tricyclo[9.3.1.0^3,8]pentadec-11-ene-1,2,5,9,10,13-hexaol
• 英文别名: (1S,2S,3R,5S,8R,9R,10R,13S)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.03,8]pentadec-11-ene-1,2,5,9,10,13-hexol
• CAS: 138613-22-6
• 化学式: C₂₀H₃₂O₆
• 分子量: 368.47
• InChiKey: RRAFCTVSIHVYHJ-AULKTIENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  121
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-cinnamoyltriacetyltaxicin I 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 6.5h， 以26%的产率得到(1S,2S,3R,5S,8R,9R,10R,13S)-8,12,15,15-Tetramethyl-4-methylene-tricyclo[9.3.1.0^3,8]pentadec-11-ene-1,2,5,9,10,13-hexaol
  参考文献：
  名称：

  Première hémisynthèse d'un composé de type taxane porteur d'un groupement oxétane en 4(20),5.

  摘要：

  The 1,2,9,10-diO-isopropylidene derivative of 2,4,9,10,13-pentadeacetyl-7-deacetoxybaccatin IV has been prepared in nine steps from taxine B, previously transformed in 2-alpha,9-alpha,10-beta-triacetyl-5-alpha-cinnamoyltaxicine I. The stereoselective reduction of the ketonic group in position 13 provides finally a molecule with an oxetane ring at positions 4(20),5 and the esterifiable hydroxyle in 13-alpha position, both being proved to be necessary to the antitumoral activity of the taxol.

  DOI：

  10.1016/s0040-4020(01)80721-3

文献信息

• Première hémisynthèse d'un composé de type taxane porteur d'un groupement oxétane en 4(20),5.
  作者：Laurent Ettouati、Alain Ahond、Christiane Poupat、Pierre Potier

  DOI：10.1016/s0040-4020(01)80721-3

  日期：1991.12

  The 1,2,9,10-diO-isopropylidene derivative of 2,4,9,10,13-pentadeacetyl-7-deacetoxybaccatin IV has been prepared in nine steps from taxine B, previously transformed in 2-alpha,9-alpha,10-beta-triacetyl-5-alpha-cinnamoyltaxicine I. The stereoselective reduction of the ketonic group in position 13 provides finally a molecule with an oxetane ring at positions 4(20),5 and the esterifiable hydroxyle in 13-alpha position, both being proved to be necessary to the antitumoral activity of the taxol.