(S)-3-N-(tert-butoxycarbonyl)amino-1,2-propanediol 1-palmitate | 850347-57-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-N-(tert-butoxycarbonyl)amino-1,2-propanediol 1-palmitate
• 英文别名: [(2S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl] hexadecanoate
• CAS: 850347-57-8
• 化学式: C₂₄H₄₇NO₅
• 分子量: 429.641
• InChiKey: OJYJRTXGWFQGLR-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  30
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-N-(tert-butoxycarbonyl)amino-1,2-propanediol 1-palmitate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 (S)-3-N-(tert-butoxycarbonyl)amino-1,2-propanediol 1-palmitate 2-(hentriacontane-31-carboxyl)ate
  参考文献：
  名称：

  Design and Synthesis of Asymmetric Acyclic Phospholipid Bolaamphiphiles

  摘要：

  A synthetic route was devised for the generation of asymmetric lipid bolaamphiphiles through the sequential esterification of an alkyldioic acid, bearing distinct terminal protecting groups, with propanylamine and lyso-phosphatidylcholine headgroups. Bolaamphiphile self-assembly was investigated in solvent mixes of varying polarity by nuclear magnetic resonance (NMR) and Fourier transform-infrared (FT-IR) spectroscopy, as well as in water by cryo-high-resolution scanning electron microscopy (cryo-HRSEM). We anticipate that asymmetric lipid bolaamphiphiles will provide facile building blocks for engineering a variety of unique membrane-mimetic structures.

  DOI：

  10.1021/jo048167o
• 作为产物：
  描述：

  棕榈酸 、 2-甲基-2-丙基[(2S)-2,3-二羟基丙基]氨基甲酸酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以63%的产率得到(S)-3-N-(tert-butoxycarbonyl)amino-1,2-propanediol 1-palmitate
  参考文献：
  名称：

  Design and Synthesis of Asymmetric Acyclic Phospholipid Bolaamphiphiles

  摘要：

  A synthetic route was devised for the generation of asymmetric lipid bolaamphiphiles through the sequential esterification of an alkyldioic acid, bearing distinct terminal protecting groups, with propanylamine and lyso-phosphatidylcholine headgroups. Bolaamphiphile self-assembly was investigated in solvent mixes of varying polarity by nuclear magnetic resonance (NMR) and Fourier transform-infrared (FT-IR) spectroscopy, as well as in water by cryo-high-resolution scanning electron microscopy (cryo-HRSEM). We anticipate that asymmetric lipid bolaamphiphiles will provide facile building blocks for engineering a variety of unique membrane-mimetic structures.

  DOI：

  10.1021/jo048167o