(1S,3S,7S,10R,11S,12S,16S)-3-((E)-1-(1,5-dimethyl-1H-pyrazol-3-yl)prop-1-en-2-yl)-8,8,10,12,16-pentamethyl-7,11-bis(trimethylsilyloxy)-4-oxabicyclo[14.1.0]heptadecane-5,9-dione | 1269438-98-3

• 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,3S,7S,10R,11S,12S,16S)-3-((E)-1-(1,5-dimethyl-1H-pyrazol-3-yl)prop-1-en-2-yl)-8,8,10,12,16-pentamethyl-7,11-bis(trimethylsilyloxy)-4-oxabicyclo[14.1.0]heptadecane-5,9-dione
• 英文别名: (1S,3S,7S,10R,11S,12S,16S)-3-[(E)-1-(1,5-dimethylpyrazol-3-yl)prop-1-en-2-yl]-8,8,10,12,16-pentamethyl-7,11-bis(trimethylsilyloxy)-4-oxabicyclo[14.1.0]heptadecane-5,9-dione
• CAS: 1269438-98-3
• 化学式: C₃₅H₆₂N₂O₅Si₂
• 分子量: 647.059
• InChiKey: RTLVOSFTEVADKV-AYNKWQMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.34
• 重原子数：
  44
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  79.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰丙酮酸乙酯 在 正丁基锂 、 氯化亚砜 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.5h， 生成 (1S,3S,7S,10R,11S,12S,16S)-3-((Z)-1-(1,5-dimethyl-1H-pyrazol-3-yl)prop-1-en-2-yl)-8,8,10,12,16-pentamethyl-7,11-bis(trimethylsilyloxy)-4-oxabicyclo[14.1.0]heptadecane-5,9-dione 、 (1S,3S,7S,10R,11S,12S,16S)-3-((E)-1-(1,5-dimethyl-1H-pyrazol-3-yl)prop-1-en-2-yl)-8,8,10,12,16-pentamethyl-7,11-bis(trimethylsilyloxy)-4-oxabicyclo[14.1.0]heptadecane-5,9-dione
  参考文献：
  名称：

  Stereoselective Synthesis of 12,13-Cyclopropyl-Epothilone B and Side-Chain-Modified Variants

  摘要：

  A general strategy has been devised for the stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants thereof, which relies on late stage introduction of the heterocycle through Wittig olefination of ketone 14. Formation of the macrocycle was achieved through RCM-based ring closure and introduction of the cyclopropane moiety involved a highly selective Charette cyclopropanation of allylic alcohol 7.

  DOI：

  10.1021/ol200114k

文献信息

• Stereoselective Synthesis of 12,13-Cyclopropyl-Epothilone B and Side-Chain-Modified Variants
  作者：Raphael Schiess、Jürg Gertsch、W. Bernd Schweizer、Karl-Heinz Altmann

  DOI：10.1021/ol200114k

  日期：2011.3.18

  A general strategy has been devised for the stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants thereof, which relies on late stage introduction of the heterocycle through Wittig olefination of ketone 14. Formation of the macrocycle was achieved through RCM-based ring closure and introduction of the cyclopropane moiety involved a highly selective Charette cyclopropanation of allylic alcohol 7.