(1S,3S,7S,10R,11S,12S,16S)-8,8,10,12,16-pentamethyl-3-((E)-1-(pyrimidin-4-yl)prop-1-en-2-yl)-7,11-bis(trimethylsilyloxy)-4-oxabicyclo[14.1.0]heptadecane-5,9-dione | 1269439-00-0

• 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)-8,8,10,12,16-pentamethyl-3-((E)-1-(pyrimidin-4-yl)prop-1-en-2-yl)-7,11-bis(trimethylsilyloxy)-4-oxabicyclo[14.1.0]heptadecane-5,9-dione
• CAS: 1269439-00-0
• 化学式: C₃₄H₅₈N₂O₅Si₂
• 分子量: 631.016
• InChiKey: QKKCLRSNRSQMLZ-VTEHNYSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  43.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  87.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1S,3S,7S,10R,11S,12S,16S)-8,8,10,12,16-pentamethyl-3-((E)-1-(pyrimidin-4-yl)prop-1-en-2-yl)-7,11-bis(trimethylsilyloxy)-4-oxabicyclo[14.1.0]heptadecane-5,9-dione 在 柠檬酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以84%的产率得到(1S,3S,7S,10R,11S,12S,16S)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-((E)-1-(pyrimidin-4-yl)prop-1-en-2-yl)-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
• 作为产物：
  描述：

  (1S,3S,7S,10R,11S,12S,16S)-3-acetyl-7,11-dihydroxy-8,8,10,12,16-pentamethyl-4-oxabicyclo[14.1.0]heptadecane-5,9-dione 在 2,6-二甲基吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 55.0h， 生成 (1S,3S,7S,10R,11S,12S,16S)-8,8,10,12,16-pentamethyl-3-((Z)-1-(pyrimidin-4-yl)prop-1-en-2-yl)-7,11-bis(trimethylsilyloxy)-4-oxabicyclo[14.1.0]heptadecane-5,9-dione 、 (1S,3S,7S,10R,11S,12S,16S)-8,8,10,12,16-pentamethyl-3-((E)-1-(pyrimidin-4-yl)prop-1-en-2-yl)-7,11-bis(trimethylsilyloxy)-4-oxabicyclo[14.1.0]heptadecane-5,9-dione 、 (1S,3R,7S,10R,11S,12S,16S)-8,8,10,12,16-pentamethyl-3-((E)-1-(pyrimidin-4-yl)prop-1-en-2-yl)-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