(E,4S)-4-[[(E,2S)-6-amino-2-(phenylmethoxycarbonylamino)hex-3-enoyl]amino]-5-methylhex-2-enoic acid | 1236182-15-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E,4S)-4-[[(E,2S)-6-amino-2-(phenylmethoxycarbonylamino)hex-3-enoyl]amino]-5-methylhex-2-enoic acid
• CAS: 1236182-15-2
• 化学式: C₂₁H₂₉N₃O₅
• 分子量: 403.478
• InChiKey: VZZLKVQFCDXCQU-XJPBYDRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E,4S)-4-[[(E,2S)-6-amino-2-(phenylmethoxycarbonylamino)hex-3-enoyl]amino]-5-methylhex-2-enoic acid 在 N-羟基-7-氮杂苯并三氮唑 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 以29.5 mg的产率得到benzyl [(3E,5S,8S,9E)-5-isopropyl-2,7-dioxo-1,6-diazacyclododeca-3,9-dien-8-yl]carbamate
  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：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (E,4S)-4-[[(E,2S)-6-amino-2-(phenylmethoxycarbonylamino)hex-3-enoyl]amino]-5-methylhex-2-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

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.