(3R,4S,5R,6R)-2-((5-acetoxy-2-(4-acetoxyphenyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)oxy)-4,5-bis(benzyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydro-2H-pyran-3-yl benzoate | 1374991-29-3

• 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: (3R,4S,5R,6R)-2-((5-acetoxy-2-(4-acetoxyphenyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)oxy)-4,5-bis(benzyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydro-2H-pyran-3-yl benzoate
• CAS: 1374991-29-3
• 化学式: C₆₂H₅₈O₁₄Si
• 分子量: 1055.22
• InChiKey: CBFXIEOWFKDLTN-DNLGVDHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.09
• 重原子数：
  77.0
• 可旋转键数：
  18.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  175.49
• 氢给体数：
  1.0
• 氢受体数：
  14.0

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)-4,5-bis(benzyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydro-2H-pyran-3-yl benzoate 、 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
  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：

  5,4'-di-O-acetyl-kaempferol 、 (3R,4S,5R,6R)-3-(benzoyloxy)-4,5-bis(benzyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-yl 2-(cyclopropylethynyl)benzoate 在 三苯基膦双(三氟甲磺酰亚胺)金 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(3R,4S,5R,6R)-2-((5-acetoxy-2-(4-acetoxyphenyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)oxy)-4,5-bis(benzyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydro-2H-pyran-3-yl benzoate
  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