[(2R,3R,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[2-[3,4-bis(phenylmethoxy)phenyl]-5-hydroxy-4-oxo-7-phenylmethoxychromen-3-yl]oxyoxan-4-yl] benzoate | 1309453-96-0

• 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)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[2-[3,4-bis(phenylmethoxy)phenyl]-5-hydroxy-4-oxo-7-phenylmethoxychromen-3-yl]oxyoxan-4-yl] benzoate
• CAS: 1309453-96-0
• 化学式: C₅₅H₄₈O₁₆
• 分子量: 964.977
• InChiKey: WTEOKKPHNOEXSA-KJSPMGEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  71
• 可旋转键数：
  22
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[2-[3,4-bis(phenylmethoxy)phenyl]-5-hydroxy-4-oxo-7-phenylmethoxychromen-3-yl]oxyoxan-4-yl] benzoate 在 potassium carbonate 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 [(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：

  氯化苄 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 12.0h， 生成 [(2R,3R,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[2-[3,4-bis(phenylmethoxy)phenyl]-5-hydroxy-4-oxo-7-phenylmethoxychromen-3-yl]oxyoxan-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