methyl 5-[2-(2,6-dimethylphenoxy)-1-methylethylaminocarbonyloxy]-2,3,4-tri-O-acetyl-β-D-glucopyranuronate | 1253889-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-[2-(2,6-dimethylphenoxy)-1-methylethylaminocarbonyloxy]-2,3,4-tri-O-acetyl-β-D-glucopyranuronate
• 英文别名: methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2R)-1-(2,6-dimethylphenoxy)propan-2-yl]carbamoyloxy]oxane-2-carboxylate
• CAS: 1253889-93-8
• 化学式: C₂₅H₃₃NO₁₂
• 分子量: 539.537
• InChiKey: YPCYLWMQYOQKDY-UHOTYFSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 5-[2-(2,6-dimethylphenoxy)-1-methylethylaminocarbonyloxy]-2,3,4-tri-O-acetyl-β-D-glucopyranuronate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以38%的产率得到sodium (1'R,2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-[2(2,6-dimethylphenoxy)-1-methylethylaminocarbonyloxy]tetrahydro-2H-pyran-2-carboxylate
  参考文献：
  名称：

  First synthesis and full characterization of mexiletine N-carbonyloxy β-d-glucuronide

  摘要：

  A simple, convergent synthesis of the N-carbonyloxy beta-D-glucuronide of mexiletine (sodium salt) in moderate yield is described. The compound is now available as an authentic reference standard for analytical studies, enabling more detailed investigation on the metabolism of mexiletine. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.150
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 、 (2R)-3-(2,6-dimethylphenoxy)-2-methylpropanoic acid 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 19.0h， 以53%的产率得到methyl 5-[2-(2,6-dimethylphenoxy)-1-methylethylaminocarbonyloxy]-2,3,4-tri-O-acetyl-β-D-glucopyranuronate
  参考文献：
  名称：

  First synthesis and full characterization of mexiletine N-carbonyloxy β-d-glucuronide

  摘要：

  A simple, convergent synthesis of the N-carbonyloxy beta-D-glucuronide of mexiletine (sodium salt) in moderate yield is described. The compound is now available as an authentic reference standard for analytical studies, enabling more detailed investigation on the metabolism of mexiletine. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.150