5-O-hexanoyl-apigenin-7-yl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside | 1145669-49-3

• 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: 5-O-hexanoyl-apigenin-7-yl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[5-hexanoyloxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 1145669-49-3
• 化学式: C₅₅H₄₆O₁₅
• 分子量: 946.961
• InChiKey: JYSJKHQENVNLMZ-HYOSKDOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  70
• 可旋转键数：
  22
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  197
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  5-O-hexanoyl-apigenin-7-yl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 、 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42%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
• 作为产物：
  描述：

  5,4'-di-O-hexanoylapigenin-7-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以84%的产率得到5-O-hexanoyl-apigenin-7-yl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
  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.