(2R,4aS,6aS,8S,9aS,11S,13aS,14R,16aS,16bR)-methyl 11-acetoxy-8,14-dihydroxy-2,4a,6a,10,10,13a,16a-heptamethyl-7,15-dioxodocosahydro-8,14-epoxybenzo[6,7]cyclodeca[1,2-a]naphthalene-2-carboxylate | 1417814-25-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2R,4aS,6aS,8S,9aS,11S,13aS,14R,16aS,16bR)-methyl 11-acetoxy-8,14-dihydroxy-2,4a,6a,10,10,13a,16a-heptamethyl-7,15-dioxodocosahydro-8,14-epoxybenzo[6,7]cyclodeca[1,2-a]naphthalene-2-carboxylate
• 英文别名: methyl (1S,3S,6S,9R,11R,12S,15R,16S,19S,21S)-19-acetyloxy-1,15-dihydroxy-3,6,9,12,16,20,20-heptamethyl-2,14-dioxo-23-oxapentacyclo[13.7.1.03,12.06,11.016,21]tricosane-9-carboxylate
• CAS: 1417814-25-5
• 化学式: C₃₃H₅₀O₉
• 分子量: 590.755
• InChiKey: FANHQEAZEFGAJZ-IUSIXPGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2R,4aS,6aS,9aS,11S,13aS,16aS,16bR)-methyl 11-acetoxy-2,4a,6a,10,10,13a,16a-heptamethyl-7,8,14,15-tetraoxodocosahydrobenzo[6,7]cyclodeca[1,2-a]naphthalene-2-carboxylate 在 lithium diisopropyl amide 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以64%的产率得到(2R,4aS,6aS,8S,9aS,11S,13aS,14R,16aS,16bR)-methyl 11-acetoxy-8,14-dihydroxy-2,4a,6a,10,10,13a,16a-heptamethyl-7,15-dioxodocosahydro-8,14-epoxybenzo[6,7]cyclodeca[1,2-a]naphthalene-2-carboxylate
  参考文献：
  名称：

  Molecular Library Synthesis Using Complex Substrates: Expanding the Framework of Triterpenoids

  摘要：

  The remodeling of a natural product core framework by means of diversity-oriented synthesis (DOS) is a valuable approach to access diverse/biologically relevant chemical space and to overcome the limitations of combinatorial-type compounds. Here we provide proof of principle and a thorough conformational analysis for a general strategy whereby the inherent complexity of a starting material is used to define the regio- and stereochemical outcomes of reactions in chemical library construction. This is in contrast to the traditional DOS logic employing reaction development and catalysis to drive library diversity.

  DOI：

  10.1021/jo302211f

文献信息

• Molecular Library Synthesis Using Complex Substrates: Expanding the Framework of Triterpenoids
  作者：Vasily A. Ignatenko、Yong Han、Gregory P. Tochtrop

  DOI：10.1021/jo302211f

  日期：2013.1.18

  The remodeling of a natural product core framework by means of diversity-oriented synthesis (DOS) is a valuable approach to access diverse/biologically relevant chemical space and to overcome the limitations of combinatorial-type compounds. Here we provide proof of principle and a thorough conformational analysis for a general strategy whereby the inherent complexity of a starting material is used to define the regio- and stereochemical outcomes of reactions in chemical library construction. This is in contrast to the traditional DOS logic employing reaction development and catalysis to drive library diversity.