allyl 1-O-(4-bromobenzoyl)-β-D-glucopyranuronate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 1-O-(4-bromobenzoyl)-β-D-glucopyranuronate
• 英文别名: allyl-(4-bromophenyl-1-O-acyl)-β-D-glucuronate；prop-2-enyl (2S,3S,4S,5R,6S)-6-(4-bromobenzoyl)oxy-3,4,5-trihydroxyoxane-2-carboxylate
• 化学式: C₁₆H₁₇BrO₈
• 分子量: 417.21
• InChiKey: BGWAFLRWJXQDMX-DJUFWWRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allyl 1-O-(4-bromobenzoyl)-β-D-glucopyranuronate 在 四(三苯基膦)钯 吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 1-O-(4-bromobenzoyl)-β-D-glucopyranuronic acid
  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
• 作为产物：
  描述：

  4-溴苯甲酸 、 allyl D-glucuronate 在 N-甲基吗啉 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以59%的产率得到allyl 1-O-(4-bromobenzoyl)-β-D-glucopyranuronate
  参考文献：
  名称：

  Effective Synthesis of 1β-Acyl Glucuronides by Selective Acylation

  摘要：

  Acyl glucuronides are vital metabolites for many carboxylic acid containing drugs. We report an efficient new method for the chemical synthesis of these molecules by selective 1 beta-acylation of allyl glucuronate with carboxylic acids catalyzed by HATU and then mild deprotection through treatment with Pd(PPh3)(4) and morpholine. The method is effective for a range of aryl and alkyl carboxylic acids, including important drugs.

  DOI：

  10.1021/ol0507165

文献信息

• Effective Synthesis of 1β-Acyl Glucuronides by Selective Acylation
  作者：Jennifer A. Perrie、John R. Harding、David W. Holt、Atholl Johnston、Paul Meath、Andrew V. Stachulski

  DOI：10.1021/ol0507165

  日期：2005.6.1

  Acyl glucuronides are vital metabolites for many carboxylic acid containing drugs. We report an efficient new method for the chemical synthesis of these molecules by selective 1 beta-acylation of allyl glucuronate with carboxylic acids catalyzed by HATU and then mild deprotection through treatment with Pd(PPh3)(4) and morpholine. The method is effective for a range of aryl and alkyl carboxylic acids, including important drugs.
• A convenient synthesis of β-acyl glucuronides
  作者：Hélène Juteau、Yves Gareau、Marc Labelle

  DOI：10.1016/s0040-4039(97)00135-4

  日期：1997.3

  beta-Acyl glucuronides are readily prepared in two steps from allyl D-glucuronate 1 in 14 to 29% overall yields. (C) 1997 Elsevier Science Ltd.
• 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.