(9Z,12Z,15Z)-Octadeca-9,12,15-trienoic acid 2-hydroxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester | 651306-09-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: (9Z,12Z,15Z)-Octadeca-9,12,15-trienoic acid 2-hydroxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester
• 英文别名: [2-hydroxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypropyl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• CAS: 651306-09-1
• 化学式: C₃₅H₅₄O₁₃
• 分子量: 682.806
• InChiKey: RHLZGOJDIKDJFQ-WRQZQFBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  48
• 可旋转键数：
  28
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  170
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (9Z,12Z,15Z)-Octadeca-9,12,15-trienoic acid 2-hydroxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester 在 4-二甲氨基吡啶 、 水 、 一水合肼 、 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 6.0h， 生成 [1-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl] 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：

  2,3,4,5-tetra-O-acetyl-D-glucopyranose 在 4-二甲氨基吡啶 、 zinc(II) nitrate hexahydrate 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 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 8.0h， 生成 (9Z,12Z,15Z)-Octadeca-9,12,15-trienoic acid 2-hydroxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester
  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

文献信息

• Synthesis and anti-herpes simplex viral activity of monoglycosyl diglycerides
  作者：Wicharn Janwitayanuchit、Khanit Suwanborirux、Chamnan Patarapanich、Sunibhond Pummangura、Vimolmas Lipipun、Tirayut Vilaivan

  DOI：10.1016/j.phytochem.2003.09.008

  日期：2003.12

  Based on the discovery of antiviral beta-galactosyl diglycerides from Clinacanthus nutans leaves, 19 monoglycosyl diglycerides were synthesized and examined for inhibitory effect on herpes simplex virus types I and 2 (HSV-1, HSV-2). A study of the structure-activity relationships of the synthetic monoglycosyl diglycerides indicated that the fatty acyl moieties were critical for inhibitory action with higher activity displayed as the acyl groups became more olefinic in character. The sugar moiety was also important for anti-HSV action; however, the type of sugar (glucose or galactose) did not affect activity. The stereochemistry at C-2 of the glycerol backbone displayed no significant effect on anti-HSV activity. Among the compounds synthesized, 1,2-O-dilinolenoyl-3-O-beta-D-glucopyranosyl-sn-glycerol showed the highest inhibitory activity against HSV-1 and HSV-2 with IC50 values of 12.5 +/- 0.5 and 18.5 +/- 1.5 mug/ml, respectively. (C) 2003 Elsevier Ltd. All rights reserved.