5,7-dibenzyloxy-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3-β-D-glucosyl-4H-chromen-4-one | 477244-20-5

• 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: 5,7-dibenzyloxy-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3-β-D-glucosyl-4H-chromen-4-one
• 英文别名: 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3-β-D-glucopyranosyloxy-5,7-bisbenzyloxy-4H-chromen-4-one；5,7-dibenzyloxy-2-(3',4'-dihydroxyphenyl)-3-β-D-glucosyl-4H-chomen-4-one；2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-5,7-bis(phenylmethoxy)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 477244-20-5
• 化学式: C₄₈H₄₀O₁₂
• 分子量: 808.838
• InChiKey: HTCUNQJYCRZQMM-RLYYWKKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  60
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  163
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5,7-dibenzyloxy-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3-β-D-glucosyl-4H-chromen-4-one 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 20 % Pd(OH)2/C 、 四丁基溴化铵 、 氢气 、 potassium carbonate 、 potassium bromide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 2-(3,4二羟基苯基)-5,7-二羟基-4-氧代-4H-1-苯并吡喃-3-基-beta-D-吡喃葡糖苷酸
  参考文献：
  名称：

  Regiospecific synthesis of quercetin O-β-d-glucosylated and O-β-d-glucuronidated isomers

  摘要：

  Quercetin, the polyphenolic compound, which has the highest daily intake, is well known for its protective effects against aging diseases and has received a lot of attention for this reason. Both quercetin 3-O-beta-D-glucuronide and quercetin 3'-O-beta-D-glucuronide are human metabolites, which, together with their regioisomers, are required for biological as well as physical chemistry studies. We present here a novel synthetic route based on the sequential and selective protections of the hydroxyl functions of quercetin allowing selective glycosylation, followed by TEMPO-mediated oxidation to the glucuronide. This methodology enabled us to synthesize the five O-beta-D-glucosides and four O-beta-D-glucuronides of quercetin, including the major human metabolite, quercetin 3-O-beta-D-glucuronide. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.03.110
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 甲醇 、 sodium methylate 、 potassium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 22.5h， 生成 5,7-dibenzyloxy-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-3-β-D-glucosyl-4H-chromen-4-one
  参考文献：
  名称：

  NOVEL FLAVANONE DERIVATIVE

  摘要：

  公开号：

  EP2460810B1

文献信息

• Regio- and stereoselective synthesis of the major metabolite of quercetin, quercetin-3-O-β-d-glucuronide
  作者：Mohamed Bouktaib、Aziz Atmani、Christian Rolando

  DOI：10.1016/s0040-4039(02)01264-9

  日期：2002.8

  Protected quercetin was first transformed selectively in its 3-O-beta-D-glucoside. Further protection of the remaining phenolic hydroxyl group allows a clean oxidation of the glucoside by TEMPO/NaOCl/NaBr under phase transfer conditions into the corresponding glucuronide which was cleanly deprotected to quercetin-3-O-beta-D-glucuronide. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Design, synthesis, and biological evaluation of a novel series of quercetin diacylglucosides as potent anti-MRSA and anti-VRE agents
  作者：Abugafar M.L. Hossion、Nao Otsuka、Rafiya K. Kandahary、Tomofusa Tsuchiya、Wakano Ogawa、Akimasa Iwado、Yoshito Zamami、Kenji Sasaki

  DOI：10.1016/j.bmcl.2010.02.060

  日期：2010.9

  A series of novel quercetin diacylglucosides were designed and first synthesized by Steglich esterification on the basis of MRSA strains inhibiting natural compound A. The in vitro inhibition of different multidrug resistant bacterial strains and Escherichia coli DNA gyrase B was investigated. In the series, compound 10h was up to 128-fold more potent against vancomycin-resistant enterococci and more effective than A, which represents a promising new candidate as a potent anti-MRSA and anti-VRE agent. (C) 2010 Published by Elsevier Ltd.