6-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucuronatopyranosyl)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl bromide | 182423-88-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucuronatopyranosyl)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl bromide
• 英文别名: O²,O³,O⁴-triacetyl-O¹-(tri-O-acetyl-1-bromo-1-deoxy-α-D-glucopyranose-6-yl)-β-D-glucopyranuronic acid methyl ester；O²,O³,O⁴-Triacetyl-O¹-(tri-O-acetyl-1-brom-1-desoxy-α-D-glucopyranose-6-yl)-β-D-glucopyranuronsaeure-methylester；methyl (2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methoxy]oxane-2-carboxylate
• CAS: 182423-88-7
• 化学式: C₂₅H₃₃BrO₁₇
• 分子量: 685.431
• InChiKey: UXOMNDIGHVDSJT-JOIGTCDNSA-N

物化性质

• 沸点：
  627.7±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  212
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  6-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucuronatopyranosyl)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl bromide 在 calcium sulfate 、 氢氧化钾 、 氰化汞 、 mercury dibromide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2S,3S,4S,5R,6R)-6-[[(2R,3S,4S,5R,6S)-6-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-methoxycarbonyl-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：

  O²,O³,O⁴-triacetyl-O¹-(tetra-O-acetyl-β-D-glucopyranose-6-yl)-β-D-glucopyranuronic acid methyl ester 在 氯仿 、 氢溴酸 、 溶剂黄146 作用下， 生成 6-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucuronatopyranosyl)-2,3,4-tri-O-acetyl-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  STUDIES ON ANTIBACTERIAL IMMUNITY INDUCED BY ARTIFICIAL ANTIGENS

  摘要：

  1. 含有结构异构的醛基糖酸的氮蛋白在兔子体内引发特异的血清学和免疫学抗体。 2. 含有合成甘露-双糖和葡萄糖醛酸的偶氮苯基糖苷抗原在兔子体内引发抗体，这些抗体可在小鼠体内提供被动免疫，使其免受对致命的II型肺炎球菌的多次感染。

  DOI：

  10.1084/jem.72.1.33