5-O-hexanoyl-7-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl) apigenin | 1145669-50-6

• 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: 5-O-hexanoyl-7-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl) apigenin
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[5-hexanoyloxy-4-oxo-2-[4-[(2S,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-methyloxan-2-yl]oxyphenyl]chromen-7-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 1145669-50-6
• 化学式: C₈₂H₆₈O₂₂
• 分子量: 1405.43
• InChiKey: LDQHHUQAFVZQAG-OXRVWYMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.1
• 重原子数：
  104
• 可旋转键数：
  33
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  274
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  5-O-hexanoyl-7-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl) apigenin 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 以88%的产率得到apigenin-7-O-β-D-glucoside-4'-O-α-L-rhamnoside
  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：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 、 5-O-hexanoylapigenin-4'-yl-2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 氯仿 、 水 为溶剂， 反应 24.0h， 以71%的产率得到5-O-hexanoyl-7-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl) apigenin
  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

文献信息

• The first total synthesis of 7-O-β-d-glucopyranosyl-4′-O-α-l-rhamnopyranosyl apigenin via a hexanoyl ester-based protection strategy
  作者：Qi Gao、Gaoyan Lian、Feng Lin

  DOI：10.1016/j.carres.2008.12.016

  日期：2009.3

  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.