7-O-(heptaacetyl-β-D-cellobiosyl)apigenin | 1381874-74-3

• 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: 7-O-(heptaacetyl-β-D-cellobiosyl)apigenin
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1381874-74-3
• 化学式: C₄₁H₄₄O₂₂
• 分子量: 888.787
• InChiKey: JCHREXSVJIMRIW-UJJNTCFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  63
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  288
• 氢给体数：
  2
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 、 7-O-(heptaacetyl-β-D-cellobiosyl)apigenin 在 喹啉 、 silver carbonate 作用下， 反应 3.0h， 以84%的产率得到7-O-(heptaacetyl-β-D-cellobiosyl)-40-O-(tetraacetyl-β-D-glycosyl)apigenin
  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
• 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 、 ammonium acetate 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 水 为溶剂， 反应 32.25h， 生成 7-O-(heptaacetyl-β-D-cellobiosyl)apigenin
  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