3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl-[(2R,3R,4S,5S,6S)-6-methoxycarbonyl-3,4,5-tris(2-methylpropanoyloxy)oxan-2-yl]-dimethylazanium;trifluoromethanesulfonate | 1207167-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl-[(2R,3R,4S,5S,6S)-6-methoxycarbonyl-3,4,5-tris(2-methylpropanoyloxy)oxan-2-yl]-dimethylazanium;trifluoromethanesulfonate
• CAS: 1207167-96-1
• 化学式: CF₃O₃S*C₃₈H₅₃N₂O₉
• 分子量: 830.917
• InChiKey: FSNCXOQSTZNWRS-KXQAEQHWSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  183
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl-[(2R,3R,4S,5S,6S)-6-methoxycarbonyl-3,4,5-tris(2-methylpropanoyloxy)oxan-2-yl]-dimethylazanium;trifluoromethanesulfonate 在 水 、 lithium hydroxide 作用下， 以 甲醇 为溶剂， 以0.064 g的产率得到丙米嗪N-beta-D-葡糖苷酸
  参考文献：
  名称：

  A convenient new synthesis of quaternary ammonium glucuronides of drug molecules

  摘要：

  N-Glucuronides, of various Structural types, are frequently encountered as drug metabolites. Efficient chemical synthesis of these compounds, both as analytical standards and for toxicological investigation, is therefore an important goal. Earlier syntheses of N+-glucuronides of aliphatic tertiary amine drugs involved direct reaction of the drug molecule with a bromosugar, but yields were generally low and of poor reproducibility, with many by-products. In addition the final products were often of low stability, hindering effective isolation and purification. We now report that a stable, readily prepared glucuronic acid hemiacetal is a reliable precursor for metabolites of this type and give three pharmaceutically relevant examples. We report further on the stability of the final metabolites and the conditions required for their isolation and purification. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.113
• 作为产物：
  描述：

  methyl (2S,3S,4S,5R,6R)-6-[3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl-methylamino]-3,4,5-tris(2-methylpropanoyloxy)oxane-2-carboxylate 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 以0.158 g的产率得到3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl-[(2R,3R,4S,5S,6S)-6-methoxycarbonyl-3,4,5-tris(2-methylpropanoyloxy)oxan-2-yl]-dimethylazanium;trifluoromethanesulfonate
  参考文献：
  名称：

  A convenient new synthesis of quaternary ammonium glucuronides of drug molecules

  摘要：

  N-Glucuronides, of various Structural types, are frequently encountered as drug metabolites. Efficient chemical synthesis of these compounds, both as analytical standards and for toxicological investigation, is therefore an important goal. Earlier syntheses of N+-glucuronides of aliphatic tertiary amine drugs involved direct reaction of the drug molecule with a bromosugar, but yields were generally low and of poor reproducibility, with many by-products. In addition the final products were often of low stability, hindering effective isolation and purification. We now report that a stable, readily prepared glucuronic acid hemiacetal is a reliable precursor for metabolites of this type and give three pharmaceutically relevant examples. We report further on the stability of the final metabolites and the conditions required for their isolation and purification. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.113