methyl (2R)-2-hydroxy-4-phenylselanylbutanoate | 364337-17-7

• 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: methyl (2R)-2-hydroxy-4-phenylselanylbutanoate
• 英文别名: methyl (2R)-2-hydroxy-4-phenylselenylbutanoate
• CAS: 364337-17-7
• 化学式: C₁₁H₁₄O₃Se
• 分子量: 273.19
• InChiKey: LWRLNXSBOWZEHS-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-hydroxy-4-phenylselanylbutanoate 在 camphor-10-sulfonic acid 、 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.83h， 生成 (R)-4-Benzyl-3-{(E)-(S)-2-[(1S,2R)-1-hydroxy-2-(4-methoxy-benzyloxy)-4-phenylselanyl-butyl]-3,7-dimethyl-octa-3,6-dienoyl}-oxazolidin-2-one
  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：

  二苯基二硒醚 在 sodium tetrahydroborate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 methyl (2R)-2-hydroxy-4-phenylselanylbutanoate
  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

• 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.