apigenin-7-O-β-D-glucoside-4'-O-α-L-rhamnoside | 1145669-55-1

• 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: apigenin-7-O-β-D-glucoside-4'-O-α-L-rhamnoside
• 英文别名: 5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphenyl]chromen-4-one
• CAS: 1145669-55-1
• 化学式: C₂₇H₃₀O₁₄
• 分子量: 578.527
• InChiKey: JWESWEUFMKPWPH-PYXJVEIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  225
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  7-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4'-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)apigenin 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 以93%的产率得到apigenin-7-O-β-D-glucoside-4'-O-α-L-rhamnoside
  参考文献：
  名称：

  The efficient total synthesis of bis-glycosyl apigenin from naringenin: a greener way

  摘要：

  An efficient total synthesis of 7-O-beta-D-glucopyranosyl-4'-O-alpha-L-rhamnopyranosyl apigenin (1) was developed in only four steps from naringenin. Compared with our previously reported first total synthesis route (six steps and 19.6% overall yield), this new route contained two steps of highly regioselective glycosylation without any selective protection steps. 7,4'-di-O-beta-D-glucopyranosyl apigenin (2) was also prepared efficiently by this method. The method is environmentally friendly, economical, and provides a greener method for flavonoid synthesis starting from an inexpensive flavanone. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.08.014

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.
• The efficient total synthesis of bis-glycosyl apigenin from naringenin: a greener way
  作者：Jianli Chen、Wei Huang、Gaoyan Lian、Feng Lin

  DOI：10.1016/j.carres.2009.08.014

  日期：2009.11

  An efficient total synthesis of 7-O-beta-D-glucopyranosyl-4'-O-alpha-L-rhamnopyranosyl apigenin (1) was developed in only four steps from naringenin. Compared with our previously reported first total synthesis route (six steps and 19.6% overall yield), this new route contained two steps of highly regioselective glycosylation without any selective protection steps. 7,4'-di-O-beta-D-glucopyranosyl apigenin (2) was also prepared efficiently by this method. The method is environmentally friendly, economical, and provides a greener method for flavonoid synthesis starting from an inexpensive flavanone. (C) 2009 Elsevier Ltd. All rights reserved.