[4-[[(2S,5S)-5-[(4-ethoxycarbonyloxy-2,6-dimethylphenyl)methyl]-3,6-dioxo-1,4-bis[(1S)-1-phenylethyl]piperazin-2-yl]methyl]-3,5-dimethylphenyl] ethyl carbonate | 1185756-58-4

• 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: [4-[[(2S,5S)-5-[(4-ethoxycarbonyloxy-2,6-dimethylphenyl)methyl]-3,6-dioxo-1,4-bis[(1S)-1-phenylethyl]piperazin-2-yl]methyl]-3,5-dimethylphenyl] ethyl carbonate
• CAS: 1185756-58-4
• 化学式: C₄₄H₅₀N₂O₈
• 分子量: 734.89
• InChiKey: BDFCKQKJECCFSJ-NLTNIQRJSA-N

物化性质

• 沸点：
  866.2±65.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  54
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [4-[[(2S,5S)-5-[(4-ethoxycarbonyloxy-2,6-dimethylphenyl)methyl]-3,6-dioxo-1,4-bis[(1S)-1-phenylethyl]piperazin-2-yl]methyl]-3,5-dimethylphenyl] ethyl carbonate 在 氢碘酸 作用下， 反应 3.0h， 以100%的产率得到2',6'-二甲基-L-酪氨酸
  参考文献：
  名称：

  A highly efficient stereocontrolled synthesis of (S)-2′,6′-dimethyltyrosine [(S)-DMT]

  摘要：

  A new, practical and very convenient stereocontrolled synthesis of (S)-2',6'-dimethyltyrosine [(S)-Dmt] 4 was accomplished in a good yield, Starting from the chiral synthon 1.4-N,N-[(S)-phenylethyl]-piperazine-2,5-dione 1. The procedure, which is an extension Of our original strategy and occurs with a high level of stereoselectivity (>98%), is simple and inexpensive allowing LIS to prepare the unnatural alpha-aminoacid (S)-Dmt also on a multi-gram scale. (C) 2009 ElsevieF Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.06.004
• 作为产物：
  描述：

  4-iodomethyl-3,5-dimethylphenyl ethyl carbonate 、 1,4-bis((S)-1-phenylethyl)piperazine-2,5-dione 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 [4-[[(2S,5S)-5-[(4-ethoxycarbonyloxy-2,6-dimethylphenyl)methyl]-3,6-dioxo-1,4-bis[(1S)-1-phenylethyl]piperazin-2-yl]methyl]-3,5-dimethylphenyl] ethyl carbonate
  参考文献：
  名称：

  A highly efficient stereocontrolled synthesis of (S)-2′,6′-dimethyltyrosine [(S)-DMT]

  摘要：

  A new, practical and very convenient stereocontrolled synthesis of (S)-2',6'-dimethyltyrosine [(S)-Dmt] 4 was accomplished in a good yield, Starting from the chiral synthon 1.4-N,N-[(S)-phenylethyl]-piperazine-2,5-dione 1. The procedure, which is an extension Of our original strategy and occurs with a high level of stereoselectivity (>98%), is simple and inexpensive allowing LIS to prepare the unnatural alpha-aminoacid (S)-Dmt also on a multi-gram scale. (C) 2009 ElsevieF Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.06.004