3-[(1R,2R)-2-[(2S,4R)-4-benzyl-5-oxooxolan-2-yl]-2-hydroxy-1-phenylethyl]sulfanylpropanamide | 180858-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-[(1R,2R)-2-[(2S,4R)-4-benzyl-5-oxooxolan-2-yl]-2-hydroxy-1-phenylethyl]sulfanylpropanamide
• CAS: 180858-15-5
• 化学式: C₂₂H₂₅NO₄S
• 分子量: 399.511
• InChiKey: GBBDZTZKJGFAAJ-KOUHRCEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  H-Val-NH(CH2)2OMe 、 3-[(1R,2R)-2-[(2S,4R)-4-benzyl-5-oxooxolan-2-yl]-2-hydroxy-1-phenylethyl]sulfanylpropanamide 在 三甲基铝 作用下， 生成 (2R,4S,5R,6R)-6-(2-cyano-ethylsulfanyl)-4,5-dihydroxy-2-benzyl-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-benzyl-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：

  (S)-4-Hydroxy-4-((2R,3S)-3-phenyl-oxiranyl)-butyric acid tert-butyl ester 在 potassium tert-butylate 、 三乙基铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.83h， 生成 3-[(1R,2R)-2-[(2S,4R)-4-benzyl-5-oxooxolan-2-yl]-2-hydroxy-1-phenylethyl]sulfanylpropanamide
  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

文献信息

• Stereoselective synthesis of (4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-γ-lactone
  作者：Arlette Solladié-Cavallo、Didier Roche、Guido Bold、Figan Acemoglu、Marina Tintelnot-Blomley、Jean Fischer、André De Cian

  DOI：10.1016/0957-4166(96)00215-7

  日期：1996.6

  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