6-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucuronatopyranosyl)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose | 35906-41-3

• 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)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: O²,O³,O⁴-triacetyl-O¹-(O¹,O²;O³,O⁴-diisopropylidene-α-D-galactopyranose-6-yl)-β-D-glucopyranuronic acid methyl ester；O²,O³,O⁴-Triacetyl-O¹-(O¹,O²;O³,O⁴-diisopropyliden-α-D-galactopyranose-6-yl)-β-D-glucopyranuronsaeure-methylester；methyl (2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxane-2-carboxylate
• CAS: 35906-41-3
• 化学式: C₂₅H₃₆O₁₅
• 分子量: 576.552
• InChiKey: KROBILRARDALOQ-AFCKXHHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  6-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucuronatopyranosyl)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose 在 氢溴酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 37.0h， 生成 6-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucuronatopyranosyl)-2,3,4-tri-O-acetyl-α-D-galactopyranosyl bromide
  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：

  O1-D-galactose-6-yl-β-D-glucopyranuronic acid methyl ester 在 硫酸 、 丙酮 作用下， 生成 6-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucuronatopyranosyl)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Levene; Tipson, Journal of Biological Chemistry, 1938, vol. 125, p. 355,360

  摘要：

  DOI：

文献信息

• Hotchkiss; Goebel, Journal of Biological Chemistry, 1936, vol. 115, p. 285,289
  作者：Hotchkiss、Goebel

  DOI：——

  日期：——