(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 | 1357286-92-0

• 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: (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
• CAS: 1357286-92-0
• 化学式: C₅₃H₈₈O₁₄
• 分子量: 949.273
• InChiKey: QKUVSEDXRLRCQC-UZIGWYEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.39
• 重原子数：
  67.0
• 可旋转键数：
  40.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  176.26
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-β-D-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy-2’,3’,4’,6’-tetracetyl]galactose 在 4-二甲氨基吡啶 、 zinc(II) nitrate hexahydrate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 (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
  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