[(1R,2R,3R,4R,5S,6S,8S,10S,11S,12R,18R)-4,5-diacetyloxy-6,10-dimethoxy-12-(methoxymethyl)-14-oxido-14-azoniapentacyclo[10.3.3.12,5.01,11.03,8]nonadec-13-en-18-yl] acetate | 1264885-79-1

• 英文名称: [(1R,2R,3R,4R,5S,6S,8S,10S,11S,12R,18R)-4,5-diacetyloxy-6,10-dimethoxy-12-(methoxymethyl)-14-oxido-14-azoniapentacyclo[10.3.3.12,5.01,11.03,8]nonadec-13-en-18-yl] acetate
• CAS: 1264885-79-1
• 化学式: C₂₈H₄₁NO₁₀
• 分子量: 551.634
• InChiKey: JADRJLLKUMFLRT-BGDYUFDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(1R,2R,3R,4R,5S,6S,8S,10S,11S,12R,18R)-4,5-diacetyloxy-6,10-dimethoxy-12-(methoxymethyl)-14-oxido-14-azoniapentacyclo[10.3.3.12,5.01,11.03,8]nonadec-13-en-18-yl] acetate 在 periodic acid dihydrate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以28%的产率得到methyl (1R,2R,3R,4R,5S,6S,8S,10S,13R,14R,17S)-4,5,14-triacetyloxy-6-methoxy-13-(methoxymethyl)-12-oxo-11-oxapentacyclo[8.6.1.12,5.03,8.013,17]octadecane-1-carboxylate
  参考文献：
  名称：

  Conversional studies towards taxoids from C₁₉-diterpenoid alkaloids by the BAC sequence

  摘要：

  The conversional synthesis of taxoids by the BAC sequence from the C19-diterpenoid alkaloids, 14-acetyltalatisamine (1), yunaconitine (12), and 14-acetylchasmanine (19), was designed and explored. Two aconane-type diterpenes 17 and 28, the advanced intermediates for our conversional synthesis, were synthesized. The key steps include the rupture of the C(7)-C(17) bond, the formation of imine, and the denitrogenation.

  DOI：

  10.1080/10286020.2010.510796
• 作为产物：
  描述：

  [(1R,2R,3R,4R,5S,6S,8S,10S,11S,12R,18R)-4,5-diacetyloxy-6,10-dimethoxy-12-(methoxymethyl)-14-azapentacyclo[10.3.3.12,5.01,11.03,8]nonadec-13-en-18-yl] acetate 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以89%的产率得到[(1R,2R,3R,4R,5S,6S,8S,10S,11S,12R,18R)-4,5-diacetyloxy-6,10-dimethoxy-12-(methoxymethyl)-14-oxido-14-azoniapentacyclo[10.3.3.12,5.01,11.03,8]nonadec-13-en-18-yl] acetate
  参考文献：
  名称：

  Conversional studies towards taxoids from C₁₉-diterpenoid alkaloids by the BAC sequence

  摘要：

  The conversional synthesis of taxoids by the BAC sequence from the C19-diterpenoid alkaloids, 14-acetyltalatisamine (1), yunaconitine (12), and 14-acetylchasmanine (19), was designed and explored. Two aconane-type diterpenes 17 and 28, the advanced intermediates for our conversional synthesis, were synthesized. The key steps include the rupture of the C(7)-C(17) bond, the formation of imine, and the denitrogenation.

  DOI：

  10.1080/10286020.2010.510796