(S,Z)-methyl 5-(tert-butyldimethylsilyloxy)-2-methyl-6-oxohept-2-enoate | 1269438-78-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S,Z)-methyl 5-(tert-butyldimethylsilyloxy)-2-methyl-6-oxohept-2-enoate
• 英文别名: methyl (Z,5S)-5-[tert-butyl(dimethyl)silyl]oxy-2-methyl-6-oxohept-2-enoate
• CAS: 1269438-78-9
• 化学式: C₁₅H₂₈O₄Si
• 分子量: 300.47
• InChiKey: BOZDXRDHSKRFRT-FUWURINLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S,Z)-methyl 5-(tert-butyldimethylsilyloxy)-2-methyl-6-oxohept-2-enoate 在 草酰氯 、 diethylzinc 、 二异丁基氢化铝 、 对甲苯磺酸 、 二甲基亚砜 、 原甲酸三乙酯 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 7.17h， 生成 (1S,2S)-2-((S)-2-(tert-butyldimethylsilyloxy)-2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-1-methylcyclopropanecarbaldehyde
  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：

  (-)-(3S)-3-{[叔-丁基(二甲基)硅烷基]氧基}二氢呋喃-2(3H)-酮 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.5h， 生成 (S,Z)-methyl 5-(tert-butyldimethylsilyloxy)-2-methyl-6-oxohept-2-enoate
  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.