methyl 3-O-[6'-O-(methyl 2'',3'',4''-tri-O-acetyl-β-D-glucuronatopyranosyl)-2',4',6'-tri-O-acetyl-β-D-galactopyranosyl]glycyrrhetinate | 182424-00-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 3-O-[6'-O-(methyl 2'',3'',4''-tri-O-acetyl-β-D-glucuronatopyranosyl)-2',4',6'-tri-O-acetyl-β-D-galactopyranosyl]glycyrrhetinate
• CAS: 182424-00-6
• 化学式: C₅₆H₈₀O₂₁
• 分子量: 1089.24
• InChiKey: ROSYFQKBPPRAID-SXTXNIPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  77.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  264.39
• 氢给体数：
  0.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-[6'-O-(methyl 2'',3'',4''-tri-O-acetyl-β-D-glucuronatopyranosyl)-2',4',6'-tri-O-acetyl-β-D-galactopyranosyl]glycyrrhetinate 在 2,4,6-三甲基吡啶 、 lithium iodide 作用下， 反应 2.0h， 以44%的产率得到(2S,3S,4S,5R,6R)-6-[[(2R,3R,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of glycyrrhetic acid diglycosides and their cytoprotective activities against CCl4--induced hepatic injury in vitro

  摘要：

  Glycyrrhetic acid diglycosides 16, 24, 25, 42 and 46, with respectively beta-D-glucuronopyranosyl-(1-->3)-beta-D-glucopyranose, -(1-->6)-alpha-D-glucopyranose, -(1-->6)-beta-D-glucopyranose, -(1-->6)-beta-D-galactopyranose, and beta-D-galacturonopyranosyl-(-->2)-beta-D-glucopyranose as sugar components at the O-3 positions on the aglycons, were synthesized. In vitro cytoprotective activities, against CCl4-induced hepatic injury, of the synthetic diglycosides, methyl beta-D-glucuronopyranosyl-(1-->4)-alpha-D-glucopyranosyl-D-glycyrrhetinate 33 and methyl esters 15 and 23 (the precursors of 16 and 24 respectively) were compared with those of glycyrrhizin 1 and beta-D-glucuronopyranosyl-(1-->2)-beta-D-glucopyranosyl-glycyrrhetic acid 2. Of the glycosides 16, 24, and 25, with beta-D-glucuronopyranosyl-glucopyranose as the sugar component, 16 and 24 were as cytoprotective as 1 and 2, whereas 25 showed no remarkable activity. From stereomodels of the glycosides these differences in activity were inferred to be due to the stereochemistries of the terminal beta-D-glucuronopyranoses in the molecules. Glycoside 46, in which the terminal beta-D-glucuronopyranose of 2 was replaced by beta-D-galacturonopyranose, was as potent as 2. Further, it was confirmed that a free COOH group on the E ring of aglycon was essential for the activity.

  DOI：

  10.1016/0223-5234(96)89552-3
• 作为产物：
  描述：

  methyl (2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3S,4S,5R)-3,4,5,6-tetraacetyloxyoxan-2-yl]methoxy]oxane-2-carboxylate 在 calcium sulfate 、 氢溴酸 、 氰化汞 、 溶剂黄146 、 mercury dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 methyl 3-O-[6'-O-(methyl 2'',3'',4''-tri-O-acetyl-β-D-glucuronatopyranosyl)-2',4',6'-tri-O-acetyl-β-D-galactopyranosyl]glycyrrhetinate
  参考文献：
  名称：

  Synthesis of glycyrrhetic acid diglycosides and their cytoprotective activities against CCl4--induced hepatic injury in vitro

  摘要：

  Glycyrrhetic acid diglycosides 16, 24, 25, 42 and 46, with respectively beta-D-glucuronopyranosyl-(1-->3)-beta-D-glucopyranose, -(1-->6)-alpha-D-glucopyranose, -(1-->6)-beta-D-glucopyranose, -(1-->6)-beta-D-galactopyranose, and beta-D-galacturonopyranosyl-(-->2)-beta-D-glucopyranose as sugar components at the O-3 positions on the aglycons, were synthesized. In vitro cytoprotective activities, against CCl4-induced hepatic injury, of the synthetic diglycosides, methyl beta-D-glucuronopyranosyl-(1-->4)-alpha-D-glucopyranosyl-D-glycyrrhetinate 33 and methyl esters 15 and 23 (the precursors of 16 and 24 respectively) were compared with those of glycyrrhizin 1 and beta-D-glucuronopyranosyl-(1-->2)-beta-D-glucopyranosyl-glycyrrhetic acid 2. Of the glycosides 16, 24, and 25, with beta-D-glucuronopyranosyl-glucopyranose as the sugar component, 16 and 24 were as cytoprotective as 1 and 2, whereas 25 showed no remarkable activity. From stereomodels of the glycosides these differences in activity were inferred to be due to the stereochemistries of the terminal beta-D-glucuronopyranoses in the molecules. Glycoside 46, in which the terminal beta-D-glucuronopyranose of 2 was replaced by beta-D-galacturonopyranose, was as potent as 2. Further, it was confirmed that a free COOH group on the E ring of aglycon was essential for the activity.

  DOI：

  10.1016/0223-5234(96)89552-3