(2S)-2-[(1S,2R)-2-p-methoxybenzyloxy-1-trimethylsilyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoic acid methoxy-N-methyl-amide | 364337-23-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S)-2-[(1S,2R)-2-p-methoxybenzyloxy-1-trimethylsilyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoic acid methoxy-N-methyl-amide
• 英文别名: (2S,3E)-N-methoxy-2-[(1S,2R)-2-[(4-methoxyphenyl)methoxy]-1-trimethylsilyloxybut-3-enyl]-N,3,7-trimethylocta-3,6-dienamide
• CAS: 364337-23-5
• 化学式: C₂₇H₄₃NO₅Si
• 分子量: 489.728
• InChiKey: KHKGILUMXZXRQF-ZGSJXCQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(1S,2R)-2-p-methoxybenzyloxy-1-trimethylsilyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoic acid methoxy-N-methyl-amide 在 titanium(IV) isopropylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 (4R,5S,6S)-4-p-methoxybenzyloxy-5-trimethylsilyloxy-6-[(E)-1,5-dimethyl-hex-1,4-dienyl]-cyclohex-2-enone
  参考文献：
  名称：

  A New, Ring Closing Metathesis-Based Synthesis of (−)-Fumagillol

  摘要：

  [GRAPHICS]A new strategy to access the fumagillin/fumagillol skeleton is proposed. An Evans aldolization and a RCM involving an enone are used for the preparation of a key cyclohexanone intermediate, which was readily converted to fumagillol. The synthesis also features an efficient preparation of isogeraniol and isogeranic acid.

  DOI：

  10.1021/ol016343z
• 作为产物：
  描述：

  2,6-二甲基-2,5-辛二烯-8-醇 在 chromium(VI) oxide 、 4-二甲氨基吡啶 、 硫酸 、 三甲基铝 、 四丁基高碘酸铵 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 、 水 、 丙酮 、 甲苯 为溶剂， 反应 7.33h， 生成 (2S)-2-[(1S,2R)-2-p-methoxybenzyloxy-1-trimethylsilyloxy-but-3-enyl]-3,7-dimethyloct-3,6-dienoic acid methoxy-N-methyl-amide
  参考文献：
  名称：

  A New, Ring Closing Metathesis-Based Synthesis of (−)-Fumagillol

  摘要：

  [GRAPHICS]A new strategy to access the fumagillin/fumagillol skeleton is proposed. An Evans aldolization and a RCM involving an enone are used for the preparation of a key cyclohexanone intermediate, which was readily converted to fumagillol. The synthesis also features an efficient preparation of isogeraniol and isogeranic acid.

  DOI：

  10.1021/ol016343z

文献信息

• A New, Ring Closing Metathesis-Based Synthesis of (−)-Fumagillol
  作者：Jean-Guy Boiteau、Pierre Van de Weghe、Jacques Eustache

  DOI：10.1021/ol016343z

  日期：2001.8.1

  [GRAPHICS]A new strategy to access the fumagillin/fumagillol skeleton is proposed. An Evans aldolization and a RCM involving an enone are used for the preparation of a key cyclohexanone intermediate, which was readily converted to fumagillol. The synthesis also features an efficient preparation of isogeraniol and isogeranic acid.