(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(3-(((9Z,12Z,15Z)-octadeca-9,12,15-trienoyl)oxy)-2-(stearoyloxy)propoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1357286-87-3

• 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-(3-(((9Z,12Z,15Z)-octadeca-9,12,15-trienoyl)oxy)-2-(stearoyloxy)propoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1357286-87-3
• 化学式: C₅₃H₈₈O₁₄
• 分子量: 949.273
• InChiKey: DKEXNTOTVGSVTK-OQMZEYQVSA-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-(3-(((9Z,12Z,15Z)-octadeca-9,12,15-trienoyl)oxy)-2-(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80%的产率得到1-O-linolenoyl-2-O-stearoyl-3-O-β-D-galactopyranosylglycerol
  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：

  3-O-(β-D-2',3',4',6'-tetra-O-acetyl-galactopyranosyl)-rac-glycerol 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， 生成 (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(3-(((9Z,12Z,15Z)-octadeca-9,12,15-trienoyl)oxy)-2-(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