(3R,5S)-3-(4-Methoxy-benzyl)-5-((2R,3S)-3-phenyl-oxiranyl)-dihydro-furan-2-one | 180858-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3R,5S)-3-(4-Methoxy-benzyl)-5-((2R,3S)-3-phenyl-oxiranyl)-dihydro-furan-2-one
• CAS: 180858-14-4
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: AMQYRLUKJGQFMR-XGXHKWSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  48.06
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3R,5S)-3-(4-Methoxy-benzyl)-5-((2R,3S)-3-phenyl-oxiranyl)-dihydro-furan-2-one 在 三甲基铝 、 三乙基铝 作用下， 反应 0.5h， 生成 (2R,4S,5R,6R)-6-(2-cyano-ethylsulfanyl)-4,5-dihydroxy-2-(4-methoxybenzyl)-6-phenyl-hexanoic acid [(1S)-1-(2-methoxy-ethylcarbamoyl)-2-methyl-propyl]-amide
  参考文献：
  名称：

  Stereoselective synthesis of (4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-γ-lactone

  摘要：

  A short (7 steps) and efficient (45% overall yield) synthesis of (4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-gamma-lactone, a versatile intermediate toward possible HIV-1 protease inhibitors, is described. Two examples of trans-alpha-benzylation of the lactonic ring followed by a regioselective opening of the epoxide (with thiopropanamide) as well as an opening of the lactone ring with L-valine (2-methoxy-ethyl)-amide are also given. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00215-7
• 作为产物：
  描述：

  (E)-(S)-4-Hydroxy-6-phenyl-hex-5-enoic acid tert-butyl ester 在 potassium tert-butylate 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 (3R,5S)-3-(4-Methoxy-benzyl)-5-((2R,3S)-3-phenyl-oxiranyl)-dihydro-furan-2-one
  参考文献：
  名称：

  Stereoselective synthesis of (4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-γ-lactone

  摘要：

  A short (7 steps) and efficient (45% overall yield) synthesis of (4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-gamma-lactone, a versatile intermediate toward possible HIV-1 protease inhibitors, is described. Two examples of trans-alpha-benzylation of the lactonic ring followed by a regioselective opening of the epoxide (with thiopropanamide) as well as an opening of the lactone ring with L-valine (2-methoxy-ethyl)-amide are also given. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00215-7