2,3,5-tri-O-benzoyl-α/β-D-apiofuranosyl bromide | 1309453-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,5-tri-O-benzoyl-α/β-D-apiofuranosyl bromide
• 英文别名: [(3R,4R)-3,4-dibenzoyloxy-5-bromooxolan-3-yl]methyl benzoate
• CAS: 1309453-93-7
• 化学式: C₂₆H₂₁BrO₇
• 分子量: 525.353
• InChiKey: JWZQXXHUGSTNHX-DCFJUCRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzoyl-α/β-D-apiofuranosyl bromide 、 [(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 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以52%的产率得到[(3S,4R,5S)-3,4-dibenzoyloxy-5-[(2S,3R,4S,5R,6R)-4-benzoyloxy-2-[2-[3,4-bis(phenylmethoxy)phenyl]-4-oxo-5,7-bis(phenylmethoxy)chromen-3-yl]oxy-5-hydroxy-6-[[(2R,3R,4R,5S,6S)-3,4,5-tribenzoyloxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl]oxyoxolan-3-yl]methyl 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：

  3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside 在 吡啶 、 甲酸 、 氢溴酸 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 18.0h， 生成 2,3,5-tri-O-benzoyl-α/β-D-apiofuranosyl bromide
  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.