3,7-di-O-benzyl-kaempferol | 1254191-99-5

• 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: 3,7-di-O-benzyl-kaempferol
• 英文别名: 3,7-Bis(benzyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one；5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis(phenylmethoxy)chromen-4-one
• CAS: 1254191-99-5
• 化学式: C₂₉H₂₂O₆
• 分子量: 466.49
• InChiKey: DQEVWRURDKDOAM-UHFFFAOYSA-N

物化性质

• 沸点：
  733.0±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,7-di-O-benzyl-kaempferol 在 吡啶 、 4-二甲氨基吡啶 、 三苯基膦双(三氟甲磺酰亚胺)金 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 作用下， 以 二氯甲烷 为溶剂， 生成 (3R,4S,5R,6R)-2-((5-acetoxy-2-(4-acetoxyphenyl)-4-oxo-7-(((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-3-yl)oxy)-6-((benzoyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  参考文献：
  名称：

  Efficient synthesis of kaempferol 3,7-O-bisglycosides via successive glycosylation with glycosyl ortho-alkynylbenzoates and trifluoroacetimidates

  摘要：

  Selective glycosylation of the 3-OH of 5,4'-di-O-acetyl-kaempferol was achieved with glycosyl orthoalkynylbenzoates as donors under the catalysis of Ph(3)PALINTf(2), and subsequent glycosylation of the remaining 7-OH with glycosyl trifluoroacetimidates under the catalysis of BF3.OEt2, after global deprotection, afforded the kaempferol 3,7-O-bisglycosides conveniently. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.103
• 作为产物：
  描述：

  山奈酚 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以40%的产率得到3,7-di-O-benzyl-kaempferol
  参考文献：
  名称：

  Efficient synthesis of kaempferol 3,7-O-bisglycosides via successive glycosylation with glycosyl ortho-alkynylbenzoates and trifluoroacetimidates

  摘要：

  Selective glycosylation of the 3-OH of 5,4'-di-O-acetyl-kaempferol was achieved with glycosyl orthoalkynylbenzoates as donors under the catalysis of Ph(3)PALINTf(2), and subsequent glycosylation of the remaining 7-OH with glycosyl trifluoroacetimidates under the catalysis of BF3.OEt2, after global deprotection, afforded the kaempferol 3,7-O-bisglycosides conveniently. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.103

文献信息

• 有机硫脲催化的酚羟基糖苷化方法
  申请人：江西师范大学

  公开号：CN113121619B

  公开（公告）日：2023-06-09

  本发明公开一种有机硫脲催化的酚羟基糖苷化方法，包括以下步骤：有机溶剂中，以糖基N‑苯基‑三氟乙酰亚胺酯为给体，以酚类化合物为受体，在Kass试剂催化下，发生糖苷化反应，得到酚糖苷。本发明方法条件温和、反应高效、易操作且选择性高。
• PHOSPHORYLATED AND PHOSPHONATED PYRONE ANALOGS FOR THERAPEUTIC TREATMENT
  申请人：Lee May Dean-Ming

  公开号：US20100297020A1

  公开（公告）日：2010-11-25

  Methods are described for the treatment and prevention of metabolic disorders or other diseases by administering a pyrone analog or a derivative thereof. Methods are also described for the treatment and prevention of metabolic disorders and other diseases by administering a pyrone analog, or a derivative thereof, in combination with one or more additional agents such as, for example, lipid lowering agents or glucose lowering agents. Methods are described for the modulation of lipid transporter activity to increase the efflux of lipid from a physiological compartment into an external environment. Methods disclosed herein may be used to assess treatment or prevention of a metabolic disorder following administration of a pyrone analog or a derivative thereof.

  本文描述了通过给予吡喃类似物或其衍生物的方法来治疗和预防代谢性疾病或其他疾病。还描述了通过给予吡喃类似物或其衍生物与一个或多个额外的药物如降脂药或降糖药组合的方法来治疗和预防代谢性疾病和其他疾病。本文还描述了调节脂质转运蛋白活性以增加生理区域中脂质向外部环境的外流的方法。本文所披露的方法可用于评估在给予吡喃类似物或其衍生物后治疗或预防代谢性疾病的效果。
• [EN] PHOSPHORYLATED AND PHOSPHONATED PYRONE ANALOGS FOR THERAPEUTIC TREATMENT<br/>[FR] ANALOGUES DE PYRONE PHOSPHORYLÉE ET PHOSPHOLATÉE POUR TRAITEMENT THÉRAPEUTIQUE
  申请人：LIMERICK BIOPHARMA

  公开号：WO2010129138A2

  公开（公告）日：2010-11-11

  Methods are described for the treatment and prevention of metabolic disorders or other diseases by administering a pyrone analog or a derivative thereof Methods are also described for the treatment and prevention of metabolic disorders and other diseases by administering a pyrone analog, or a derivative thereof, in combination with one or more additional agents such as, for example, lipid lowering agents or glucose lowering agents Methods are described for the modulation of lipid transporter activity to increase the efflux of lipid from a physiological compartment into an external environment Methods disclosed herein may be used to assess treatment or prevention of a metabolic disorder following administration of a pyrone analog or a derivative thereof.
• Efficient synthesis of kaempferol 3,7-O-bisglycosides via successive glycosylation with glycosyl ortho-alkynylbenzoates and trifluoroacetimidates
  作者：Weizhun Yang、Jiansong Sun、Zhongyi Yang、Wei Han、Wei-Dong Zhang、Biao Yu

  DOI：10.1016/j.tetlet.2012.03.103

  日期：2012.5

  Selective glycosylation of the 3-OH of 5,4'-di-O-acetyl-kaempferol was achieved with glycosyl orthoalkynylbenzoates as donors under the catalysis of Ph(3)PALINTf(2), and subsequent glycosylation of the remaining 7-OH with glycosyl trifluoroacetimidates under the catalysis of BF3.OEt2, after global deprotection, afforded the kaempferol 3,7-O-bisglycosides conveniently. (C) 2012 Elsevier Ltd. All rights reserved.