4',7-di-O-benzyl-3-O-(β-D-glucopyranosyl)quercetin | 6743-87-9

• 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: 4',7-di-O-benzyl-3-O-(β-D-glucopyranosyl)quercetin
• 英文别名: 7,4'-Dibenzyl-quercetin-3-mono-β-D-glucosid；5-hydroxy-2-(3-hydroxy-4-phenylmethoxyphenyl)-7-phenylmethoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 6743-87-9
• 化学式: C₃₅H₃₂O₁₂
• 分子量: 644.632
• InChiKey: FSOSEFAAWSCECZ-YCDISTCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  185
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4',7-di-O-benzyl-3-O-(β-D-glucopyranosyl)quercetin 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以98%的产率得到异槲皮苷
  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：

  槲皮素 在 吡啶 、 sodium methylate 、 potassium carbonate 、 potassium iodide 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 169.0h， 生成 4',7-di-O-benzyl-3-O-(β-D-glucopyranosyl)quercetin
  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

• Synthesis of Quercetin 3-<i>O</i>-[6^″-<i>O</i>-(<i>trans</i>-<i>p</i>-Coumaroyl)]-<i>β</i>-D-Glucopyranoside
  作者：Xuhong Ren、Liu-lan Shen、Osamu Muraoka、Maosheng Cheng

  DOI：10.1080/07328303.2011.616979

  日期：2011.4

  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.