3-{(1R,2R)-2-Hydroxy-2-[(2S,4R)-4-(4-methoxy-benzyl)-5-oxo-tetrahydro-furan-2-yl]-1-phenyl-ethylsulfanyl}-propionamide | 180858-16-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-{(1R,2R)-2-Hydroxy-2-[(2S,4R)-4-(4-methoxy-benzyl)-5-oxo-tetrahydro-furan-2-yl]-1-phenyl-ethylsulfanyl}-propionamide
• CAS: 180858-16-6
• 化学式: C₂₃H₂₇NO₅S
• 分子量: 429.537
• InChiKey: HTQGJIBMVDHREN-HGIWEUDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  98.85
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  H-Val-NH(CH2)2OMe 、 3-{(1R,2R)-2-Hydroxy-2-[(2S,4R)-4-(4-methoxy-benzyl)-5-oxo-tetrahydro-furan-2-yl]-1-phenyl-ethylsulfanyl}-propionamide 在 三甲基铝 作用下， 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 、 (2R,4S,5R,6R)-6-(2-carbamoyl-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：

  1-(碘甲基)-4-甲氧基苯 在 三乙基铝 、 lithium diisopropyl amide 作用下， 反应 1.33h， 生成 3-{(1R,2R)-2-Hydroxy-2-[(2S,4R)-4-(4-methoxy-benzyl)-5-oxo-tetrahydro-furan-2-yl]-1-phenyl-ethylsulfanyl}-propionamide
  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