benzyl α-D-glucuronate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl α-D-glucuronate
• 英文别名: D-glucuronic acid benzyl ester；benzyl alpha-D-glucopyranuronate；benzyl (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
• 化学式: C₁₃H₁₆O₇
• 分子量: 284.266
• InChiKey: MYEUFSLWFIOAGY-SVNGYHJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  D-吡喃葡萄糖醛酸 、 溴甲苯 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 benzyl α-D-glucuronate 、 benzyl-D-glucuronate
  参考文献：
  名称：

  一种新的蔗糖酯类化学酶催化途径

  摘要：

  蔗糖酯是最发达的碳水化合物酯，应用于食品、化妆品和制药行业。在这里，我们介绍了一种新的化学酶促途径，用于合成 β-D-呋喃果糖基-(2,1)-α-D-糖醛酸衍生物，一类新的蔗糖酯。

  DOI：

  10.1002/ejoc.201701313

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.
• A Chemoenzymatic Route to a Class of Sucrose Esters
  作者：Christian Possiel、Alexandra Bäuerle、Jürgen Seibel

  DOI：10.1002/ejoc.201701313

  日期：2017.11.16

  Sucrose esters are the most developed carbohydrate esters and applied in food, cosmetic and pharmaceutical industries. Here we introduce a novel chemoenzymatic pathway for the synthesis of β-D-fructofuranosyl-(2,1)-α-D-uronic acid derivatives, a new class of sucrose esters.

  蔗糖酯是最发达的碳水化合物酯，应用于食品、化妆品和制药行业。在这里，我们介绍了一种新的化学酶促途径，用于合成 β-D-呋喃果糖基-(2,1)-α-D-糖醛酸衍生物，一类新的蔗糖酯。