[(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 | 1309453-94-8

• 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: [(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
• CAS: 1309453-94-8
• 化学式: C₅₆H₄₈O₁₃
• 分子量: 928.989
• InChiKey: QMPLXHFAZASXCO-YIDWVCFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  69
• 可旋转键数：
  19
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  169
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(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 、 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到[(2S,3S,4R,5R,6R)-4,5-dibenzoyloxy-6-[[(2R,3R,4S,5R,6S)-4-benzoyloxy-6-[2-[3,4-bis(phenylmethoxy)phenyl]-4-oxo-5,7-bis(phenylmethoxy)chromen-3-yl]oxy-3,5-dihydroxyoxan-2-yl]methoxy]-2-methyloxan-3-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：

  芦丁 在 盐酸 、 四丁基溴化铵 、 potassium carbonate 、 乙酰氯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 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

文献信息

• Synthesis of quercetin 3-O-β-d-apiofuranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranoside
  作者：Yang Zhang、Kejun Wang、Zhilai Zhan、Yu Yang、Yimin Zhao

  DOI：10.1016/j.tetlet.2011.04.040

  日期：2011.6

  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.