(S)-3-N-(tert-butoxycarbonyl)amino-1,2-propanediol 1-palmitate 2-(31-benzyloxycarbonyl-16-hentriaconten)oate | 850347-59-0

• 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: (S)-3-N-(tert-butoxycarbonyl)amino-1,2-propanediol 1-palmitate 2-(31-benzyloxycarbonyl-16-hentriaconten)oate
• 英文别名: 1-O-benzyl 32-O-[(2S)-1-hexadecanoyloxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]propan-2-yl] (Z)-dotriacont-16-enedioate
• CAS: 850347-59-0
• 化学式: C₆₃H₁₁₁NO₈
• 分子量: 1010.58
• InChiKey: KYUUAIYHMYPVHO-HEOCJGITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.2
• 重原子数：
  72
• 可旋转键数：
  56
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-3-N-(tert-butoxycarbonyl)amino-1,2-propanediol 1-palmitate 2-(31-benzyloxycarbonyl-16-hentriaconten)oate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 202.0h， 生成 [(2R)-2-[32-[(2S)-1-amino-3-hexadecanoyloxypropan-2-yl]oxy-32-oxodotriacontanoyl]oxy-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
  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：

  16-iodohexadecanoic acid 在 4-二甲氨基吡啶 、 lithium hydroxide 、 正丁基锂 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 氯仿 为溶剂， 反应 70.67h， 生成 (S)-3-N-(tert-butoxycarbonyl)amino-1,2-propanediol 1-palmitate 2-(31-benzyloxycarbonyl-16-hentriaconten)oate
  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

文献信息

• Design and Synthesis of Asymmetric Acyclic Phospholipid Bolaamphiphiles
  作者：Toshitsugu Kai、Xue-Long Sun、Keith M. Faucher、Robert P. Apkarian、Elliot L. Chaikof

  DOI：10.1021/jo048167o

  日期：2005.4.1

  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.