7-O-β-D-cellobiosyl-4'-O-β-D-glycosylapigenin

• 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-β-D-cellobiosyl-4'-O-β-D-glycosylapigenin
• 英文别名: 7-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
• 化学式: C₃₃H₄₀O₂₀
• 分子量: 756.669
• InChiKey: NVYCRSROJRTVQP-TZFWSYDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  53
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  324
• 氢给体数：
  12
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  (S)-柚皮素 在 喹啉 、 甲醇 、 silver carbonate 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 potassium methanolate 、 ammonium acetate 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 氯仿 、 水 为溶剂， 反应 37.25h， 生成 7-O-β-D-cellobiosyl-4'-O-β-D-glycosylapigenin
  参考文献：
  名称：

  The first total synthesis of apigenin 7-O-β-D-cellobiosyl-4′-O-β-D-glucopyranoside isolated from Salvia uliginosa

  摘要：

  The first total synthesis of apigenin 7-O--D-cellobioside (5) and apigenin 7-O--D-cellobiosyl-4-O--D-glucopyranoside (8), which were isolated from petals of Salvia patens and Salvia uliginosa, were achieved in four and six steps and 76% and 57%, respectively, overall yield, from naringenin (1). The total synthesis contained two-glycosylation, acetylation, oxidation, selective deacetylation and deprotection steps. Although this route contained six steps, the targeted compounds were obtained with higher yields and easier purifications than other synthetic methods.

  DOI：

  10.1080/14786419.2012.686908

文献信息

• The first total synthesis of apigenin 7-<i>O</i>-β-<scp>D</scp>-cellobiosyl-4′-<i>O</i>-β-<scp>D</scp>-glucopyranoside isolated from <i>Salvia uliginosa</i>
  作者：Fatih Sonmez、Mehmet Nebioglu、Senol Besoluk、Mustafa Arslan、Mustafa Zengin、Mustafa Kucukislamoglu

  DOI：10.1080/14786419.2012.686908

  日期：2013.4.1

  The first total synthesis of apigenin 7-O--D-cellobioside (5) and apigenin 7-O--D-cellobiosyl-4-O--D-glucopyranoside (8), which were isolated from petals of Salvia patens and Salvia uliginosa, were achieved in four and six steps and 76% and 57%, respectively, overall yield, from naringenin (1). The total synthesis contained two-glycosylation, acetylation, oxidation, selective deacetylation and deprotection steps. Although this route contained six steps, the targeted compounds were obtained with higher yields and easier purifications than other synthetic methods.