(1S,3S,7S,10R,11S,12S,16S)-7,11-bis(tert-butyldimethylsilyloxy)-8,8,10,12,16-pentamethyl-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxabicyclo[14.1.0]heptadecane-5,9-dione | 1269438-92-7

• 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)-7,11-bis(tert-butyldimethylsilyloxy)-8,8,10,12,16-pentamethyl-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxabicyclo[14.1.0]heptadecane-5,9-dione
• CAS: 1269438-92-7
• 化学式: C₃₇H₇₀O₇Si₂
• 分子量: 683.13
• InChiKey: KISYWYXFMSLSQK-KAAQTLONSA-N

物化性质

• 熔点：
  64-67 °C
• 沸点：
  648.2±55.0 °C(predicted)
• 密度：
  1.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  46.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  80.29
• 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)-7,11-bis(tert-butyldimethylsilyloxy)-8,8,10,12,16-pentamethyl-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxabicyclo[14.1.0]heptadecane-5,9-dione 在 iron(III) chloride hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以94%的产率得到(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
  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,16R,E)-7,11-bis(tert-butyldimethylsilyloxy)-8,8,10,12,16-pentamethyl-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxabicyclo[14.1.0]heptadec-13-ene-5,9-dione 在 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、750.01 kPa 条件下， 反应 14.0h， 以80%的产率得到(1S,3S,7S,10R,11S,12S,16S)-7,11-bis(tert-butyldimethylsilyloxy)-8,8,10,12,16-pentamethyl-3-(2-methyl-1,3-dioxolan-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