(4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-γ-lactone | 175879-16-0

• 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: (4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-γ-lactone
• 英文别名: (5S)-5-[(2R,3S)-3-phenyloxiran-2-yl]oxolan-2-one
• CAS: 175879-16-0
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: RAXHFHHNYGNXQO-ZMLRMANQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-γ-lactone 在 三甲基铝 、 三乙基铝 、 lithium diisopropyl amide 作用下， 反应 1.33h， 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
  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 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (4S,5R,6S)-4-(5,6-epoxy-6-phenyl)-γ-lactone
  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

• Effect of a Phosphazene Base on the Diastereoselectivity of Addition of α-Sulfonyl Carbanions to Butyraldehyde and Isopropylideneglyceraldehyde
  作者：Arlette Solladié-Cavallo、Didier Roche、Jean Fischer、André De Cian

  DOI：10.1021/jo9518967

  日期：1996.1.1

  additions of thus formed "naked" alpha-sulfonyl carbanions to achiral butyraldehyde and chiral isopropylideneglyceraldehyde was studied. It has been found that with tBuP4 a reasonable yield ( approximately 55%) and a slightly better diastereoselectivity (72% of the anti diastreomer) are obtained with achiral and nonfunctionalized butyraldehyde while with isopropylideneglyceraldehyde the use of tBuP4 allowed

  研究了tBuP4（一种强而无阳离子的碱）对如此形成的“裸”α-磺酰基碳负离子向非手性丁醛和手性异亚丙基甘油醛添加的收率和非对映选择性的影响。已经发现，使用tBuP4时，使用非手性和非官能化丁醛可获得合理的收率（约55％）和非对映选择性（稍高的抗非对映异构体的72％），而使用异亚丙基甘油醛则可大大提高收率（高达95-100％）和非对映选择性（单个非对映异构体占四种可能的非对映异构体的83-89％）。还显示出在α位的额外氧原子在该效应中起决定作用。