[2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] octadecanoate | 1357286-94-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: [2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] octadecanoate
• CAS: 1357286-94-2
• 化学式: C₄₅H₈₀O₁₀
• 分子量: 781.124
• InChiKey: UHPLILYACSUFNX-PTHUHPFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  55
• 可旋转键数：
  38
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(((9Z,12Z,15Z)-octadeca-9,12,15-trienoyl)oxy)-3-(stearoyloxy)propoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 水 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以77%的产率得到[2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] octadecanoate
  参考文献：
  名称：

  An efficient and versatile chemical synthesis of bioactive glyco-glycerolipids

  摘要：

  Synthesis of beta-glyco-1,2-diacylglycerols is achieved by a versatile and simple procedure based on trichloro-acetimidate methodology and use of peracetate sugar substrates. The chemical strategy was tested through stereoselective preparation of beta-galacto- and beta-gluco-lipid derivatives capable to trigger immune system response. The synthetic approach is designed to obtain enantiomerically pure regio- and stereo-isomers including derivatives containing poly-unsaturated fatty acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.030