1'-(methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-2'-[(3',4'-isopropylidene)phenyl]ethanol | 1185745-19-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1'-(methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-2'-[(3',4'-isopropylidene)phenyl]ethanol
• 英文别名: methyl (2S,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[2-(2,2-dimethyl-1,3-benzodioxol-5-yl)ethoxy]oxane-2-carboxylate
• CAS: 1185745-19-0
• 化学式: C₃₉H₃₆O₁₂
• 分子量: 696.708
• InChiKey: WELUYNQXMBARPI-OBIZPLPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  51
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1'-(methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-2'-[(3',4'-isopropylidene)phenyl]ethanol 在 水 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 96.0h， 生成
  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
• 作为产物：
  描述：

  2-(2,2-dimethylbenzo[1,3]dioxol-5-yl)ethanol 、 methyl 2,3,4-tri-O-benzoyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以84%的产率得到1'-(methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-2'-[(3',4'-isopropylidene)phenyl]ethanol
  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

文献信息

• A concise synthesis of glucuronide metabolites of urolithin-B, resveratrol, and hydroxytyrosol
  作者：Ricardo Lucas、David Alcantara、Juan Carlos Morales

  DOI：10.1016/j.carres.2009.05.016

  日期：2009.7

  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.