[(2R,3R,4S,5R,6S)-6-[5-acetyloxy-2-(4-acetyloxyphenyl)-4-oxo-3-[(2S,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-methyloxan-2-yl]oxychromen-7-yl]oxy-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate | 1374991-35-1

• 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: [(2R,3R,4S,5R,6S)-6-[5-acetyloxy-2-(4-acetyloxyphenyl)-4-oxo-3-[(2S,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-methyloxan-2-yl]oxychromen-7-yl]oxy-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 1374991-35-1
• 化学式: C₈₀H₆₂O₂₄
• 分子量: 1407.36
• InChiKey: NXSDGDDAKVDANB-BDTXZRPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  104
• 可旋转键数：
  31
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  300
• 氢给体数：
  0
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  [(2S,3S,4R,5R,6S)-6-[5-acetyloxy-2-(4-acetyloxyphenyl)-7-hydroxy-4-oxochromen-3-yl]oxy-4,5-dibenzoyloxy-2-methyloxan-3-yl] benzoate 、 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl N-phenyltrifluoroacetimidate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到[(2R,3R,4S,5R,6S)-6-[5-acetyloxy-2-(4-acetyloxyphenyl)-4-oxo-3-[(2S,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-methyloxan-2-yl]oxychromen-7-yl]oxy-3,4,5-tribenzoyloxyoxan-2-yl]methyl 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