(3R,4S,5R,6R)-2-((5-acetoxy-2-(4-acetoxyphenyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)oxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate | 1374991-28-2

• 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: (3R,4S,5R,6R)-2-((5-acetoxy-2-(4-acetoxyphenyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)oxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• CAS: 1374991-28-2
• 化学式: C₅₃H₄₀O₁₇
• 分子量: 948.89
• InChiKey: YYJWKAHEPQMLQO-REBVYXBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.65
• 重原子数：
  70.0
• 可旋转键数：
  14.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  226.7
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R,6R)-2-((5-acetoxy-2-(4-acetoxyphenyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)oxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 、 2,3,4-tri-O-acetyl-L-rhamnopyranosyl (N-phenyl)-2,2,2-trifluoroacetimidate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到(3R,4S,5R,6R)-2-((5-acetoxy-2-(4-acetoxyphenyl)-4-oxo-7-(((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-3-yl)oxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  参考文献：
  名称：

  Efficient synthesis of kaempferol 3,7-O-bisglycosides via successive glycosylation with glycosyl ortho-alkynylbenzoates and trifluoroacetimidates

  摘要：

  Selective glycosylation of the 3-OH of 5,4'-di-O-acetyl-kaempferol was achieved with glycosyl orthoalkynylbenzoates as donors under the catalysis of Ph(3)PALINTf(2), and subsequent glycosylation of the remaining 7-OH with glycosyl trifluoroacetimidates under the catalysis of BF3.OEt2, after global deprotection, afforded the kaempferol 3,7-O-bisglycosides conveniently. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.103
• 作为产物：
  描述：

  山奈酚 在 吡啶 、 4-二甲氨基吡啶 、 三苯基膦双(三氟甲磺酰亚胺)金 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (3R,4S,5R,6R)-2-((5-acetoxy-2-(4-acetoxyphenyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)oxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  参考文献：
  名称：

  Efficient synthesis of kaempferol 3,7-O-bisglycosides via successive glycosylation with glycosyl ortho-alkynylbenzoates and trifluoroacetimidates

  摘要：

  Selective glycosylation of the 3-OH of 5,4'-di-O-acetyl-kaempferol was achieved with glycosyl orthoalkynylbenzoates as donors under the catalysis of Ph(3)PALINTf(2), and subsequent glycosylation of the remaining 7-OH with glycosyl trifluoroacetimidates under the catalysis of BF3.OEt2, after global deprotection, afforded the kaempferol 3,7-O-bisglycosides conveniently. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.103