7-O-benzyl-5-O-hexanoylapigenin-4'-yl-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside | 1145669-53-9

• 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: 7-O-benzyl-5-O-hexanoylapigenin-4'-yl-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside
• CAS: 1145669-53-9
• 化学式: C₅₅H₄₈O₁₃
• 分子量: 916.978
• InChiKey: AKFXFIBFRSOFLH-FOLGJZITSA-N

物化性质

• 沸点：
  981.2±65.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.33
• 重原子数：
  68.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  163.1
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  7-O-benzyl-5-O-hexanoylapigenin-4'-yl-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside 在 甲酸 、 10% Pd on charcoal 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 45.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 以79%的产率得到5-O-hexanoylapigenin-4'-yl-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  The first total synthesis of 7-O-β-d-glucopyranosyl-4′-O-α-l-rhamnopyranosyl apigenin via a hexanoyl ester-based protection strategy

  摘要：

  The first total synthesis of 7-O-beta-D-glucopyranosyl-4 '-O-alpha-L-rhamnopyranosyI apigenin 1, which exhibits good anti-hepatitis B virus and anti-stroke activities, was accomplished in six steps and 20% overall yield from apigenin. Another synthetic route, in which the target was obtained in seven steps, was also developed to prove the utility of a hexanoyl ester-based orthogonal protection strategy. The hexanoyl protection strategy provided all the flavonoid intermediates with good solubility and reactivity, enabled efficient selective protection and glycosylation, and provided a practical and effective synthetic strategy for flavonoids, starting from commercially available flavone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.016
• 作为产物：
  描述：

  7-O-benzyl-5-O-hexanoyl apigenin 、 2,3,4-O-tribenzoyl-α,β-L-rhamnopyranoside 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以63%的产率得到7-O-benzyl-5-O-hexanoylapigenin-4'-yl-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  The first total synthesis of 7-O-β-d-glucopyranosyl-4′-O-α-l-rhamnopyranosyl apigenin via a hexanoyl ester-based protection strategy

  摘要：

  The first total synthesis of 7-O-beta-D-glucopyranosyl-4 '-O-alpha-L-rhamnopyranosyI apigenin 1, which exhibits good anti-hepatitis B virus and anti-stroke activities, was accomplished in six steps and 20% overall yield from apigenin. Another synthetic route, in which the target was obtained in seven steps, was also developed to prove the utility of a hexanoyl ester-based orthogonal protection strategy. The hexanoyl protection strategy provided all the flavonoid intermediates with good solubility and reactivity, enabled efficient selective protection and glycosylation, and provided a practical and effective synthetic strategy for flavonoids, starting from commercially available flavone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.016