3,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-5-β-D-glucopyranosyloxy-4H-chromen-4-one | 40554-90-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-5-β-D-glucopyranosyloxy-4H-chromen-4-one
• CAS: 40554-90-3
• 化学式: C₄₉H₄₄O₁₂
• 分子量: 824.881
• InChiKey: HTSSYTUQBIXXOD-MWHMJSQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.95
• 重原子数：
  61.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  166.51
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-5-β-D-glucopyranosyloxy-4H-chromen-4-one 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 20 % Pd(OH)2/C 、 四丁基溴化铵 、 氢气 、 potassium carbonate 、 potassium bromide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 quercetin 5-O-β-D-glucuronide
  参考文献：
  名称：

  Regiospecific synthesis of quercetin O-β-d-glucosylated and O-β-d-glucuronidated isomers

  摘要：

  Quercetin, the polyphenolic compound, which has the highest daily intake, is well known for its protective effects against aging diseases and has received a lot of attention for this reason. Both quercetin 3-O-beta-D-glucuronide and quercetin 3'-O-beta-D-glucuronide are human metabolites, which, together with their regioisomers, are required for biological as well as physical chemistry studies. We present here a novel synthetic route based on the sequential and selective protections of the hydroxyl functions of quercetin allowing selective glycosylation, followed by TEMPO-mediated oxidation to the glucuronide. This methodology enabled us to synthesize the five O-beta-D-glucosides and four O-beta-D-glucuronides of quercetin, including the major human metabolite, quercetin 3-O-beta-D-glucuronide. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.03.110
• 作为产物：
  描述：

  3,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-5-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranosyloxy-4H-chromen-4-one 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以82%的产率得到3,7-bisbenzyloxy-2-(3,4-bisbenzyloxyphenyl)-5-β-D-glucopyranosyloxy-4H-chromen-4-one
  参考文献：
  名称：

  Regiospecific synthesis of quercetin O-β-d-glucosylated and O-β-d-glucuronidated isomers

  摘要：

  Quercetin, the polyphenolic compound, which has the highest daily intake, is well known for its protective effects against aging diseases and has received a lot of attention for this reason. Both quercetin 3-O-beta-D-glucuronide and quercetin 3'-O-beta-D-glucuronide are human metabolites, which, together with their regioisomers, are required for biological as well as physical chemistry studies. We present here a novel synthetic route based on the sequential and selective protections of the hydroxyl functions of quercetin allowing selective glycosylation, followed by TEMPO-mediated oxidation to the glucuronide. This methodology enabled us to synthesize the five O-beta-D-glucosides and four O-beta-D-glucuronides of quercetin, including the major human metabolite, quercetin 3-O-beta-D-glucuronide. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.03.110