(2S,3S,4R,5R,6R)-2-[[4-[(3-methylimidazol-3-ium-1-yl)methyl]phenyl]methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol;hexafluorophosphate | 1312423-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R,6R)-2-[[4-[(3-methylimidazol-3-ium-1-yl)methyl]phenyl]methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol;hexafluorophosphate
• CAS: 1312423-97-4
• 化学式: C₃₉H₄₃N₂O₆*F₆P
• 分子量: 780.744
• InChiKey: HQYKRVLWBUFYCH-AGEQOVPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.73
• 重原子数：
  54
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R,6R)-2-[[4-[(3-methylimidazol-3-ium-1-yl)methyl]phenyl]methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol;hexafluorophosphate 、 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以86.8%的产率得到4-[(1-methylimidazoliumhexafluorophospho)methyl]benzyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Assembly of Homolinear α(1→2)-Linked Nonamannoside on Ionic Liquid Support

  摘要：

  An improved method for the synthesis of large and complex oligosaccharides on ionic liquid (IL) support was developed. A strategy to attach the acceptor on IL using a more stable ether linker was used to prevent undesirable decomposition and side products. A "dissolution-evaporation-precipitation" purification procedure was also developed by combining the advantages of precipitation and solid-liquid extraction to reduce mechanical loss and purification time. This approach was successfully used for the rapid assembly of ionic liquid supported homolinear alpha(1 -> 2)-linked nonamannoside in 25.2% overall yield within 28.5 h.

  DOI：

  10.1021/jo2006126
• 作为产物：
  描述：

  4-(bromomethyl)benzyl alcohol acetate 在 六氟磷酸钾 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.25h， 生成 (2S,3S,4R,5R,6R)-2-[[4-[(3-methylimidazol-3-ium-1-yl)methyl]phenyl]methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol;hexafluorophosphate
  参考文献：
  名称：

  Assembly of Homolinear α(1→2)-Linked Nonamannoside on Ionic Liquid Support

  摘要：

  An improved method for the synthesis of large and complex oligosaccharides on ionic liquid (IL) support was developed. A strategy to attach the acceptor on IL using a more stable ether linker was used to prevent undesirable decomposition and side products. A "dissolution-evaporation-precipitation" purification procedure was also developed by combining the advantages of precipitation and solid-liquid extraction to reduce mechanical loss and purification time. This approach was successfully used for the rapid assembly of ionic liquid supported homolinear alpha(1 -> 2)-linked nonamannoside in 25.2% overall yield within 28.5 h.

  DOI：

  10.1021/jo2006126

文献信息

• An efficient ionic liquid supported divergent assembly of 3,6-branched glucosamine-containing pentasaccharide
  作者：Ze-Shen Gao、Sheng Sun、Wei Li、Qing Ma、Qing Li、Zhong-Jun Li

  DOI：10.1016/j.cclet.2014.09.016

  日期：2014.12

  We utilized the glycosyl acceptor tagging method with ionic liquid support for synthesis of the core segment of Clostridium botulinum C2 toxin ligand through a divergent synthetic strategy without chromatographic purification. The total yield was 57.1% and the reaction was completed in 10 h. The efficient ionic liquid supported glycosylation and purification procedure was applied for the synthesis of branched glucosamine-containing oligosaccharides for the first time, which expanded the scope of ionic liquid supported synthesis of biologically important oligosaccharides. (C) 2014 Qing Li and Zhong-Jun Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Assembly of Homolinear α(1→2)-Linked Nonamannoside on Ionic Liquid Support
  作者：Qing Ma、Sheng Sun、Xiang-Bao Meng、Qing Li、Shu-Chun Li、Zhong-Jun Li

  DOI：10.1021/jo2006126

  日期：2011.7.15

  An improved method for the synthesis of large and complex oligosaccharides on ionic liquid (IL) support was developed. A strategy to attach the acceptor on IL using a more stable ether linker was used to prevent undesirable decomposition and side products. A "dissolution-evaporation-precipitation" purification procedure was also developed by combining the advantages of precipitation and solid-liquid extraction to reduce mechanical loss and purification time. This approach was successfully used for the rapid assembly of ionic liquid supported homolinear alpha(1 -> 2)-linked nonamannoside in 25.2% overall yield within 28.5 h.