(-)-[1S(1R*,5S*,9S*,10S*,11S*,12R*,13R*)7E]-1-hydroxy-9-methoxy-7,10,12-trimethyl-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-13-[(trimethylsilyl)oxy]-4,15-dioxabicyclo[9.3.1]pentadec-7-en-3-one | 1112362-13-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (-)-[1S(1R*,5S*,9S*,10S*,11S*,12R*,13R*)7E]-1-hydroxy-9-methoxy-7,10,12-trimethyl-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-13-[(trimethylsilyl)oxy]-4,15-dioxabicyclo[9.3.1]pentadec-7-en-3-one
• 英文别名: (1S,5R,7E,9R,10R,11S,12S,13S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-hydroxy-9-methoxy-7,10,12-trimethyl-13-trimethylsilyloxy-4,15-dioxabicyclo[9.3.1]pentadec-7-en-3-one
• CAS: 1112362-13-6
• 化学式: C₂₇H₅₂O₇Si₂
• 分子量: 544.877
• InChiKey: HGIMREAYSPKWCN-QZMQROITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (-)-6-{[2S-(2R*,3R*,4R*,5R*,6S*,10S*),7E]-4,10-dihydroxy-6-methoxy-3,5,8-trimethyl-11-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-[(trimethylsilyl)oxy]-undec-7-enyl}-2,2-dimethyl-4H-1,3-dioxin-4-one 以 苯 为溶剂， 反应 12.0h， 以76%的产率得到(-)-[1S(1R*,5S*,9S*,10S*,11S*,12R*,13R*)7E]-1-hydroxy-9-methoxy-7,10,12-trimethyl-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-13-[(trimethylsilyl)oxy]-4,15-dioxabicyclo[9.3.1]pentadec-7-en-3-one
  参考文献：
  名称：

  通过酰基乙烯酮的双大内酯化/吡喃-半缩酮形成：在合成（-）-callipeltoside A和lyngbyaloside B模型系统中的应用。

  摘要：

  Thermal generation of acylketenes in diol-containing substrates results in dual macrocyclization/pyran-hemiketal formation. This transformation expands the scope of acylketene macrolactonizations and their application to the synthesis of complex macrolides. Triol and even tetrol substrates also have been closed in highly regioselective fashion. Additionally, the challenging macrolactonization of a tertiary alcohol was achieved.

  DOI：

  10.1002/anie.200804049

文献信息

• Dual Macrolactonization/Pyran-Hemiketal Formation via Acylketenes: Applications to the Synthesis of (−)-Callipeltoside A and a Lyngbyaloside B Model System
  作者：Thomas R. Hoye、Michael E. Danielson、Aaron E. May、Hongyu Zhao

  DOI：10.1002/anie.200804049

  日期：2008.12.1

  Thermal generation of acylketenes in diol-containing substrates results in dual macrocyclization/pyran-hemiketal formation. This transformation expands the scope of acylketene macrolactonizations and their application to the synthesis of complex macrolides. Triol and even tetrol substrates also have been closed in highly regioselective fashion. Additionally, the challenging macrolactonization of a tertiary alcohol was achieved.