(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 | 1417814-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• 英文别名: methyl (1S,5S,7S,10S,14S,15R,17R,20S)-7-acetyloxy-1,6,6,10,14,17,20-heptamethyl-2,3,11,12-tetraoxotetracyclo[12.8.0.05,10.015,20]docosane-17-carboxylate
• CAS: 1417814-22-2
• 化学式: C₃₃H₄₈O₈
• 分子量: 572.739
• InChiKey: POGUSXDWAIHNTE-JNIIXZPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  41
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-methyl 10-acetoxy-2,4a,6a,9,9,12a,14a-heptamethyl-7,13-dioxo-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-2-carboxylate 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 以18%的产率得到(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
  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