2-ethyl-O-(3',4'-dihydroxyphenyl)methyl-β-D-glucopyranosyluronate | 889363-98-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-ethyl-O-(3',4'-dihydroxyphenyl)methyl-β-D-glucopyranosyluronate
• 英文别名: 2-(3',4'-dihydroxyphenyl)ethanol-1-O-β-D-glucuronide；(2S,3S,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 889363-98-8
• 化学式: C₁₄H₁₈O₉
• 分子量: 330.292
• InChiKey: PBFRPJWCYVIGKI-BYNIDDHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 水 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以42 mg的产率得到2-ethyl-O-(3',4'-dihydroxyphenyl)methyl-β-D-glucopyranosyluronate
  参考文献：
  名称：

  A concise synthesis of glucuronide metabolites of urolithin-B, resveratrol, and hydroxytyrosol

  摘要：

  A simple and direct strategy to chemically synthesize O-beta-D-glucuronides of urolithin-B 4, resveratrol 5, and the corresponding hydroxytyrosol derivatives 6, 7 (as a regioisomeric mixture), and 8 is described. The critical glycosylation step has been optimized using a structurally simple phenol, urolithin-B, by modification of several reaction parameters (solvent, promoter, and glucuronide donor). Very high yields have been obtained in the first synthesis of the O-beta-D-glucuronide of urolithin-B 4. Extension of these reaction conditions was used for the synthesis of resveratrol-3-O-glucuronide 5 where a higher yield than previously reported was obtained by using the much more common trichloroacetimidate glucuronide donor. Finally, three O-beta-D-glucuronides of hydroxytyrosol 6, 7, and 8 have been synthesized for the first time using chemical synthesis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.05.016