3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol | 131021-81-3

• 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: 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol
• 英文别名: 4'-7-di-O-benzylquercet-3-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；4',7-di-O-benzyl-3-O-(β-D-2,3,4,6-tetra-acetylglucopyranosyl)quercetin；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[5-hydroxy-2-(3-hydroxy-4-phenylmethoxyphenyl)-4-oxo-7-phenylmethoxychromen-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 131021-81-3
• 化学式: C₄₃H₄₀O₁₆
• 分子量: 812.781
• InChiKey: SMWULZNQWDFXBO-BBUWPEJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  59
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  209
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol 在 palladium 10% on activated carbon 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 反应 9.5h， 生成 异槲皮苷
  参考文献：
  名称：

  Synthesis of Quercetin 3-O-[6^″-O-(trans-p-Coumaroyl)]-β-D-Glucopyranoside

  摘要：

  This report describes the efficient synthesis of quercetin 3-O-[6 ''-O-(trans-pcoumaroyl)]-beta-D-glucopyranoside 1 (isoquercitrin coumarate), an acylated quercetin glycoside possessing antihypertensive, antidiabetic, and tyrosinase inhibitory activities. The synthesis is initiated from commercially available quercetin via regioselective benzylation of quercetin to produce 4', 7-di-O-benzylquercetin (4). Through 4, 1 was successfully achieved via selective beta-glycosylation of the 3-OH, acylation of 6 ''-OH, and finally debenzylation via catalytic transfer hydrogenation.

  DOI：

  10.1080/07328303.2011.616979
• 作为产物：
  描述：

  氯化苄 在 potassium carbonate 、 potassium iodide 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 155.5h， 生成 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol
  参考文献：
  名称：

  Synthesis of Quercetin 3-O-[6^″-O-(trans-p-Coumaroyl)]-β-D-Glucopyranoside

  摘要：

  This report describes the efficient synthesis of quercetin 3-O-[6 ''-O-(trans-pcoumaroyl)]-beta-D-glucopyranoside 1 (isoquercitrin coumarate), an acylated quercetin glycoside possessing antihypertensive, antidiabetic, and tyrosinase inhibitory activities. The synthesis is initiated from commercially available quercetin via regioselective benzylation of quercetin to produce 4', 7-di-O-benzylquercetin (4). Through 4, 1 was successfully achieved via selective beta-glycosylation of the 3-OH, acylation of 6 ''-OH, and finally debenzylation via catalytic transfer hydrogenation.

  DOI：

  10.1080/07328303.2011.616979

文献信息

• Effects of Functional Groups and Sugar Composition of Quercetin Derivatives on Their Radical Scavenging Properties
  作者：Komei Kato、Masayuki Ninomiya、Kaori Tanaka、Mamoru Koketsu

  DOI：10.1021/acs.jnatprod.6b00274

  日期：2016.7.22

  biological actions. The aim of this study was to investigate the structure–activity relationships of quercetin derivatives, with a focus on the influence of functional groups and sugar composition on their antioxidant capacity. A series of quercetin derivatives were therefore prepared and assessed for their DPPH radical scavenging properties. Isoquercetin O-gallates were more potent radical scavengers

  槲皮素衍生物广泛存在于植物界，并表现出各种生物学作用。这项研究的目的是研究槲皮素衍生物的结构-活性关系，重点是官能团和糖成分对其抗氧化能力的影响。因此，制备了一系列槲皮素衍生物，并评估了它们的DPPH自由基清除性能。异槲皮素O-加仑酸酯比槲皮素更有效的自由基清除剂。系统分析强调了异槲皮素O-没食子酸酯中羟基取代基的分布对其效能的重要性。
• Phase-transfer-catalyzed synthesis of flavonoid glycosides
  作者：Costas Demetzos、Alexios-Le´andros Skaltsounis、Franç¸ois Tillequin、Michel Koch

  DOI：10.1016/0008-6215(90)80012-r

  日期：1990.10
• DEMETZOS, COSTAS;SKALTSOUNIS, ALEXIOS-LEANDROS;TILLEQUIN, FRANCOIS;KOCH, +, CARBOHYDR. RES., 207,(1990) N, C. 131-137
  作者：DEMETZOS, COSTAS、SKALTSOUNIS, ALEXIOS-LEANDROS、TILLEQUIN, FRANCOIS、KOCH, +

  DOI：——

  日期：——