benzyl (S,E)-4-(5-methoxy-5-oxopent-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate | 1236182-10-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (S,E)-4-(5-methoxy-5-oxopent-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: benzyl (4S)-4-[(E)-5-methoxy-5-oxopent-1-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1236182-10-7
• 化学式: C₁₉H₂₅NO₅
• 分子量: 347.411
• InChiKey: SBSVQEFORNOTMS-BPLPYTOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (S,E)-4-(5-methoxy-5-oxopent-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate 在 lithium hydroxide monohydrate 、 水 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 为溶剂， 以96%的产率得到(S,E)-5-(3-(benzyloxycarbonyl)-2,2-dimethyloxazolidin-4-yl)pent-4-enoic acid
  参考文献：
  名称：

  Total Synthesis of Syringolin A

  摘要：

  A convergent, efficient synthesis of syringolin A has been accomplished in 13 steps from commercially available materials, Garner's aldehyde and L-valine. The unnatural 3,4-dehydrolysine fragment was prepared using successive Johnson-Claisen/Curtius rearrangement reactions. The macrolactamization and late-stage introduction of the side chain will provide convenient access to analogues of this promising proteasome Inhibitor.

  DOI：

  10.1021/ol101252y
• 作为产物：
  描述：

  原乙酸三甲酯 、 benzyl (4R)-4-(1-hydroxyallyl)-2,2-dimethyloxazolidine-3-carboxylate 在 丙酸 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 18.0h， 以93%的产率得到benzyl (S,E)-4-(5-methoxy-5-oxopent-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Total Synthesis of Syringolin A

  摘要：

  A convergent, efficient synthesis of syringolin A has been accomplished in 13 steps from commercially available materials, Garner's aldehyde and L-valine. The unnatural 3,4-dehydrolysine fragment was prepared using successive Johnson-Claisen/Curtius rearrangement reactions. The macrolactamization and late-stage introduction of the side chain will provide convenient access to analogues of this promising proteasome Inhibitor.

  DOI：

  10.1021/ol101252y

文献信息

• Total Synthesis of Syringolin A
  作者：Chunhui Dai、Corey R. J. Stephenson

  DOI：10.1021/ol101252y

  日期：2010.8.6

  A convergent, efficient synthesis of syringolin A has been accomplished in 13 steps from commercially available materials, Garner's aldehyde and L-valine. The unnatural 3,4-dehydrolysine fragment was prepared using successive Johnson-Claisen/Curtius rearrangement reactions. The macrolactamization and late-stage introduction of the side chain will provide convenient access to analogues of this promising proteasome Inhibitor.