(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[7-benzyloxy-2-(4-benzyloxy-3-methoxy-phenyl)-5-hydroxy-4-oxo-4H-chromen-3-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester | 906088-78-6

• 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: (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[7-benzyloxy-2-(4-benzyloxy-3-methoxy-phenyl)-5-hydroxy-4-oxo-4H-chromen-3-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[5-hydroxy-2-(3-methoxy-4-phenylmethoxyphenyl)-4-oxo-7-phenylmethoxychromen-3-yl]oxyoxane-2-carboxylate
• CAS: 906088-78-6
• 化学式: C₄₃H₄₀O₁₆
• 分子量: 812.781
• InChiKey: IIGAVQOAOVIUBJ-LELKPENRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  59
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[7-benzyloxy-2-(4-benzyloxy-3-methoxy-phenyl)-5-hydroxy-4-oxo-4H-chromen-3-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester 在 palladium dihydroxide 环己烯 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[5,7-dihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-4-oxo-4H-chromen-3-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Convenient syntheses of metabolically important quercetin glucuronides and sulfates

  摘要：

  Synthetic approaches to the major human plasma metabolites of quercetin, quercetin 3'-sulfate and the beta-D-glucopyranosiduronic acid derivatives 3'-methylquercetin 3-glucuronide (isorhamnetin 3-glucuronide), quercetin 3-glucuronide and quercetin 3'-glucuronide are described. This is the first report of the chemical synthesis of quercetin 3'-glucuronide. All procedures start from the same precursor, 4',7-di-O-benzylquercetin, and all are more convenient than existing methods. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.102
• 作为产物：
  描述：

  3'-O-methyl-4',7-di-O-benzylquercetin 、 乙酰溴-Alpha-D-葡萄糖酮酸甲基酯 在 溶剂黄146 吡啶 、 calcium sulfate 、 silver(l) oxide 作用下， 以51%的产率得到(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[7-benzyloxy-2-(4-benzyloxy-3-methoxy-phenyl)-5-hydroxy-4-oxo-4H-chromen-3-yloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Convenient syntheses of metabolically important quercetin glucuronides and sulfates

  摘要：

  Synthetic approaches to the major human plasma metabolites of quercetin, quercetin 3'-sulfate and the beta-D-glucopyranosiduronic acid derivatives 3'-methylquercetin 3-glucuronide (isorhamnetin 3-glucuronide), quercetin 3-glucuronide and quercetin 3'-glucuronide are described. This is the first report of the chemical synthesis of quercetin 3'-glucuronide. All procedures start from the same precursor, 4',7-di-O-benzylquercetin, and all are more convenient than existing methods. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.102