methyl 1,2,3,4-tetra-O-(3-fluorobenzoyl)-α-D-glucuronate | 905561-09-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 1,2,3,4-tetra-O-(3-fluorobenzoyl)-α-D-glucuronate
• CAS: 905561-09-3
• 化学式: C₃₅H₂₄F₄O₁₁
• 分子量: 696.563
• InChiKey: QWXWQHYRMLDCDJ-KVEGKNDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  50.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 1,2,3,4-tetra-O-(3-fluorobenzoyl)-α-D-glucuronate 在 无水碳酸镉 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 (2S,3S,4S,5R,6R)-3,4,5-Tris-(3-fluoro-benzoyloxy)-6-[(Z)-2-hydroxy-1-(7-methoxycarbonyl-heptyl)-dec-4-enyloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  NMR and HPLC-MS/MS analysis of synthetically prepared linoleic acid diol glucuronides

  摘要：

  Hydroxylated fatty acids are important mediators of many physiological and pathophysiological processes in a variety of human tissues. Recent evidence shows that in humans many of these are ultimately excreted in the urine as the glucuronide conjugates. In this paper we describe a general approach for the chemical synthesis of glucuronide conjugate derivatives of fatty acids. The synthesis strategy employs three steps (epoxiclation, hydrolysis and glucuronidation) using methyl linoleate as a model non-hydroxylated starting compound. Hydroxylated starting compounds would require only the glucuronidation step. NMR and HPLC-MS/MS experiments were used to help determine the structure of the synthesized glucuronide conjugates and to identify fragmentation product ions useful for discriminating positional isomers in biological samples. This synthetic strategy should prove useful for generating analytical standards in order to identify and quantify glucuronide metabolites of hydroxylated fatty acids in humans. (c) 2006 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2006.01.007
• 作为产物：
  描述：

  methyl α-D-glucuronate 、 间氟苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 24.0h， 以81%的产率得到methyl 1,2,3,4-tetra-O-(3-fluorobenzoyl)-α-D-glucuronate
  参考文献：
  名称：

  NMR and HPLC-MS/MS analysis of synthetically prepared linoleic acid diol glucuronides

  摘要：

  Hydroxylated fatty acids are important mediators of many physiological and pathophysiological processes in a variety of human tissues. Recent evidence shows that in humans many of these are ultimately excreted in the urine as the glucuronide conjugates. In this paper we describe a general approach for the chemical synthesis of glucuronide conjugate derivatives of fatty acids. The synthesis strategy employs three steps (epoxiclation, hydrolysis and glucuronidation) using methyl linoleate as a model non-hydroxylated starting compound. Hydroxylated starting compounds would require only the glucuronidation step. NMR and HPLC-MS/MS experiments were used to help determine the structure of the synthesized glucuronide conjugates and to identify fragmentation product ions useful for discriminating positional isomers in biological samples. This synthetic strategy should prove useful for generating analytical standards in order to identify and quantify glucuronide metabolites of hydroxylated fatty acids in humans. (c) 2006 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2006.01.007