(3R,4S,5S,6R,7R)-6-benzoyloxy-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-7-ethyl-1-oxaspiro[2.5]octane | 527755-15-3

• 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: (3R,4S,5S,6R,7R)-6-benzoyloxy-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-7-ethyl-1-oxaspiro[2.5]octane
• 英文别名: [(3R,4S,5S,6R,7R)-7-ethyl-5-methoxy-4-[(E)-6-methylhept-2-en-2-yl]-1-oxaspiro[2.5]octan-6-yl] benzoate
• CAS: 527755-15-3
• 化学式: C₂₅H₃₆O₄
• 分子量: 400.558
• InChiKey: QUMBCDVELQBXDO-MFVOCLFDSA-N

物化性质

• 沸点：
  499.4±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6R,7R)-6-benzoyloxy-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-7-ethyl-1-oxaspiro[2.5]octane 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以84%的产率得到(3R,4S,5S,6R,7R)-6-benzoyloxy-4-[(1R,2R)-1,2-epoxy-1,5-dimethylhexyl]-7-ethyl-5-methoxy-1-oxaspiro[2.5]octane
  参考文献：
  名称：

  MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues

  摘要：

  The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.

  DOI：

  10.1021/jo035065+
• 作为产物：
  描述：

  (E)-4-iodo-3-methylbut-3-en-1-ol 在 咪唑 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 正丁基锂 、 草酰氯 、 硫酸 、 四丁基氟化铵 、 三甲基铝 、 sodium hydride 、 四丁基高碘酸铵 、 magnesium 、 N,N-二甲基甲酰胺 、 N,N'-二环己基碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 silver(l) oxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 氯仿 、 水 、 二甲基亚砜 、 丙酮 、 甲苯 为溶剂， 反应 102.67h， 生成 (3R,4S,5S,6R,7R)-6-benzoyloxy-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-7-ethyl-1-oxaspiro[2.5]octane
  参考文献：
  名称：

  MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues

  摘要：

  The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.

  DOI：

  10.1021/jo035065+

文献信息

• MetAP-2 Inhibitors Based on the Fumagillin Structure. Side-Chain Modification and Ring-Substituted Analogues
  作者：Vincent Rodeschini、Jean-Guy Boiteau、Pierre Van de Weghe、Céline Tarnus、Jacques Eustache

  DOI：10.1021/jo035065+

  日期：2004.1.1

  The preparation of a series of new fumagillin-derived MetAP-2 inhibitors is described. The synthetic approach was designed so as to permit modification of the fumagillin backbone at sites inaccessible through semisynthesis or previously existing total syntheses. An Evans aldolization and a ring-closing metathesis allowed the preparation of a pivotal intermediate which could then be functionalized in various ways using already established or newly developed methodologies.