(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-4-(benzoyloxy)-6-((5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)tetrahydro-2H-pyran-3,5-diyl diacetate | 1309453-97-1

• 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: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-4-(benzoyloxy)-6-((5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)tetrahydro-2H-pyran-3,5-diyl diacetate
• CAS: 1309453-97-1
• 化学式: C₆₂H₅₄O₁₆
• 分子量: 1055.1
• InChiKey: IWFPMCAWECQQSO-JZCBIIKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.53
• 重原子数：
  78.0
• 可旋转键数：
  21.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  190.79
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-4-(benzoyloxy)-6-((5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)tetrahydro-2H-pyran-3,5-diyl diacetate 在 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 以82%的产率得到[(2S,3R,4S,5R,6R)-2-[2-[3,4-bis(phenylmethoxy)phenyl]-4-oxo-5,7-bis(phenylmethoxy)chromen-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] benzoate
  参考文献：
  名称：

  Synthesis of quercetin 3-O-β-d-apiofuranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranoside

  摘要：

  A concise method to construct a unique 2,6-branched trisaccharide was established by regioselective glycosylation of three free hydroxyl groups on a 3-O-protected glucose moiety, and successfully used in the synthesis of quercetin 3-O-beta-D-apiofuranosyl-(1 -> 2)-[alpha-L-rhamnopyranosyl-(1 -> 6)]-beta-D-glucopyranoside, a flavonol O-glycoside isolated from glandless cotton seeds which showed notable antidepressant activities. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.040
• 作为产物：
  描述：

  7-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-5-hydroxy-3-(((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-((((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy) methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one 在 盐酸 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-4-(benzoyloxy)-6-((5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)tetrahydro-2H-pyran-3,5-diyl diacetate
  参考文献：
  名称：

  Synthesis of quercetin 3-O-β-d-apiofuranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranoside

  摘要：

  A concise method to construct a unique 2,6-branched trisaccharide was established by regioselective glycosylation of three free hydroxyl groups on a 3-O-protected glucose moiety, and successfully used in the synthesis of quercetin 3-O-beta-D-apiofuranosyl-(1 -> 2)-[alpha-L-rhamnopyranosyl-(1 -> 6)]-beta-D-glucopyranoside, a flavonol O-glycoside isolated from glandless cotton seeds which showed notable antidepressant activities. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.040