(1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carboxylic acid methyl ester | 193271-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carboxylic acid methyl ester
• 英文别名: methyl (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.02,11.03,8]pentadec-13-ene-2-carboxylate
• CAS: 193271-84-0
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: YHGUEGWYQDELOK-KKWBWGGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carboxylic acid methyl ester 在 sodium tetrahydroborate 、 臭氧 作用下， 生成 methyl (1S,2S,3R,5S,6S,7S,9R,12R)-3,5-bis(hydroxymethyl)-7-methoxy-12-phenyl-8,11,13-trioxatricyclo[7.4.0.02,6]tridecane-2-carboxylate
  参考文献：
  名称：

  Efficient enantiospecific entry to a highly functionalized cyclopentane building block

  摘要：

  A simple and efficient route has been developed for the synthesis of a polyfunctionalized cyclopentane in enantiomerically pure form. D-Glucose is the source of chirality for this versatile building block and a highly diastereoselective Diels-Alder reaction with cyclopentadiene is the key step. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00225-5
• 作为产物：
  描述：

  (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carbaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 、 双氧水 作用下， 以 乙醚 、 乙酸乙酯 、 叔丁醇 为溶剂， 生成 (1S,2S,3S,5R,8R,10S,11S,12R)-10-methoxy-5-phenyl-4,6,9-trioxatetracyclo[10.2.1.0^2,11.0^3,8]pentadec-13-ene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Efficient enantiospecific entry to a highly functionalized cyclopentane building block

  摘要：

  A simple and efficient route has been developed for the synthesis of a polyfunctionalized cyclopentane in enantiomerically pure form. D-Glucose is the source of chirality for this versatile building block and a highly diastereoselective Diels-Alder reaction with cyclopentadiene is the key step. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00225-5

文献信息

• Unsymmetrical ozonolysis of carbohydrate derived norbornene systems
  作者：Sebastián A. Testero、María I. Mangione、Andrés A. Poeylaut-Palena、Manuel González Sierra、Rolando A. Spanevello

  DOI：10.1016/j.tet.2007.08.070

  日期：2007.11

  The ozonolysis of carbohydrate derived norbornene systems in participating solvents demonstrated that different remote controlling factors could induce the regioselective fragmentation of the primary ozonide. The exo norbornene series afforded a complete regioselective process.

  碳水化合物衍生的降冰片烯系统在参与溶剂中的臭氧分解表明，不同的远程控制因素可能会导致伯臭氧层的区域选择性断裂。在外型降冰片烯系列提供了完整的区域选择性的过程。
• Efficient enantiospecific entry to a highly functionalized cyclopentane building block
  作者：Silvina C. Pellegrinet、Rolando A. Spanevello

  DOI：10.1016/s0957-4166(97)00225-5

  日期：1997.6

  A simple and efficient route has been developed for the synthesis of a polyfunctionalized cyclopentane in enantiomerically pure form. D-Glucose is the source of chirality for this versatile building block and a highly diastereoselective Diels-Alder reaction with cyclopentadiene is the key step. (C) 1997 Elsevier Science Ltd.