(2S,3S,4S,5R,6S)-6-[2-[5-(4-氯苯甲酰基)-1,4-二甲基吡咯-2-基]乙酰基]氧基-3,4,5-三羟基四氢吡喃-2-羧酸 | 75871-31-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2S,3S,4S,5R,6S)-6-[2-[5-(4-氯苯甲酰基)-1,4-二甲基吡咯-2-基]乙酰基]氧基-3,4,5-三羟基四氢吡喃-2-羧酸
• 英文名称: Zomepirac glucuronide
• 英文别名: (2S,3S,4S,5R,6S)-6-[2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 75871-31-7
• 化学式: C₂₁H₂₂ClNO₉
• 分子量: 467.86
• InChiKey: FNGKIZYZSHHXJZ-ZFORQUDYSA-N

物化性质

• 沸点：
  692.7±55.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  156
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  佐美酸 在 palladium on activated charcoal N-甲基吗啉 、 1,4-环己二烯 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 异丙醇 、 乙腈 为溶剂， 反应 4.0h， 生成 (2S,3S,4S,5R,6S)-6-[2-[5-(4-氯苯甲酰基)-1,4-二甲基吡咯-2-基]乙酰基]氧基-3,4,5-三羟基四氢吡喃-2-羧酸
  参考文献：
  名称：

  Efficient synthesis of 1β-O-acyl glucuronides via selective acylation of allyl or benzyl d-glucuronate

  摘要：

  Acyl glucuronides are key metabolites for many carboxylic acid-containing drugs, notably those of the non-steroidal anti-inflammatory class. In the processes of drug safety assessment and new drug development, it is essential that acyl glucuronides, if formed in vivo, should be made conveniently available for bioevaluation. We recently showed that selective acylation of allyl glucuronate is a promising method for the synthesis of these metabolites in good yield and with excellent beta-anomeric selectivity. We now give fuller details of the allyl ester method and further report that benzyl glucuronate performs at least equally well in the acylation step, offering the advantage of very mild deprotection by catalytic transfer (or conventional) hydrogenation. Depending on the compatibility of other functional groups, as discussed below, this will be the method of choice for many acyl glucuronide syntheses. The value of the method is demonstrated in particular by the synthesis of several acyl glucuronides that are known metabolites of important drugs. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.050

文献信息

• Efficient synthesis of 1β-O-acyl glucuronides via selective acylation of allyl or benzyl d-glucuronate
  作者：Elizabeth R. Bowkett、John R. Harding、James L. Maggs、B. Kevin Park、Jennifer A. Perrie、Andrew V. Stachulski

  DOI：10.1016/j.tet.2007.05.050

  日期：2007.8

  Acyl glucuronides are key metabolites for many carboxylic acid-containing drugs, notably those of the non-steroidal anti-inflammatory class. In the processes of drug safety assessment and new drug development, it is essential that acyl glucuronides, if formed in vivo, should be made conveniently available for bioevaluation. We recently showed that selective acylation of allyl glucuronate is a promising method for the synthesis of these metabolites in good yield and with excellent beta-anomeric selectivity. We now give fuller details of the allyl ester method and further report that benzyl glucuronate performs at least equally well in the acylation step, offering the advantage of very mild deprotection by catalytic transfer (or conventional) hydrogenation. Depending on the compatibility of other functional groups, as discussed below, this will be the method of choice for many acyl glucuronide syntheses. The value of the method is demonstrated in particular by the synthesis of several acyl glucuronides that are known metabolites of important drugs. (C) 2007 Elsevier Ltd. All rights reserved.