beta-D-吡喃葡萄糖醛酸 1-(2-丙基戊酸酯) | 60113-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: beta-D-吡喃葡萄糖醛酸 1-(2-丙基戊酸酯)
• 中文别名: beta-D-吡喃葡萄糖醛酸1-(2-丙基戊酸酯)
• 英文名称: Valproic acid glucuronide
• 英文别名: 1-(2-propylpentanoate)-β-D-Glucopyranuronic acid；valproyl 1-O-β-acyl glucuronide；valproate-β-D-glucuronide；valproate glucuronide；VPA-G；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-propylpentanoyloxy)oxane-2-carboxylic acid
• CAS: 60113-83-9
• 化学式: C₁₄H₂₄O₈
• 分子量: 320.34
• InChiKey: XXKSYIHWRBBHIC-JVWRJRKNSA-N

物化性质

• 熔点：
  118-120°C
• 沸点：
  491.9±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  丙戊酸 在 palladium on activated charcoal 1,3-二氮杂双环[2.2.2]辛烷 、 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 3.0h， 生成 beta-D-吡喃葡萄糖醛酸 1-(2-丙基戊酸酯)
  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

• COMPOSITIONS AND METHODS FOR TREATING OBESITY AND OBESITY-RELATED CONDITIONS
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：US20150250747A1

  公开（公告）日：2015-09-10

  The present invention relates to the field of obesity. More specifically, the present invention provides methods and compositions useful in treating obesity and obesity-associated conditions. In one embodiment, a method for treating obesity in a subject comprises the step of administering an effective amount of valproic acid (VPA) or an analog, derivative or metabolite thereof to the subject.
• US9463173B2
  申请人：——

  公开号：US9463173B2

  公开（公告）日：2016-10-11
• 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.