1-methyl-3-(2-oxo-2-(((2R,3R,4S,5S,6R)-3,4,5-tris(benzoyloxy)-6-fluorotetrahydro-2H-pyran-2-yl)methoxy)ethyl)-1H-imidazol-3-ium hexafluorophosphate(V) | 1005398-17-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-methyl-3-(2-oxo-2-(((2R,3R,4S,5S,6R)-3,4,5-tris(benzoyloxy)-6-fluorotetrahydro-2H-pyran-2-yl)methoxy)ethyl)-1H-imidazol-3-ium hexafluorophosphate(V)
• CAS: 1005398-17-3
• 化学式: C₃₃H₃₀FN₂O₉*F₆P
• 分子量: 762.572
• InChiKey: NTEVDQSYQZSZSH-MOQRLPRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  52.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  123.24
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-methyl-3-(2-oxo-2-(((2R,3R,4S,5S,6R)-3,4,5-tris(benzoyloxy)-6-fluorotetrahydro-2H-pyran-2-yl)methoxy)ethyl)-1H-imidazol-3-ium hexafluorophosphate(V) 、 p-thiotolyl 2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 在 二氯二茂铪 、 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到C₉₄H₈₁N₂O₂₅S⁽¹⁺⁾*F₆P^(1-)
  参考文献：
  名称：

  Oligomannan Synthesis Using Ionic Liquid Supported Glycosylation

  摘要：

  The synthesis of complex oligosaccharides has been a challenge for researchers. Herein, we describe a strategy for the synthesis of an activated oligomannan 1 that employs ionic liquid (IL) support glycosylation methodology on an IL-tagged mannosyl fluoride donor. This method is capable of rapidly producing linear alpha(1 -> 6) oligomannan thioglycosides in a convenient and cost-effective manner without the need of column purification after each glycosylation step.

  DOI：

  10.1021/ol702743x
• 作为产物：
  描述：

  N-甲基咪唑 、 2,3,4-tri-O-benzoyl-6-O-(chloroacetyl)-α-D-mannopyranosyl fluoride 在 六氟磷酸钾 作用下， 以 乙腈 为溶剂， 以82%的产率得到1-methyl-3-(2-oxo-2-(((2R,3R,4S,5S,6R)-3,4,5-tris(benzoyloxy)-6-fluorotetrahydro-2H-pyran-2-yl)methoxy)ethyl)-1H-imidazol-3-ium hexafluorophosphate(V)
  参考文献：
  名称：

  Oligomannan Synthesis Using Ionic Liquid Supported Glycosylation

  摘要：

  The synthesis of complex oligosaccharides has been a challenge for researchers. Herein, we describe a strategy for the synthesis of an activated oligomannan 1 that employs ionic liquid (IL) support glycosylation methodology on an IL-tagged mannosyl fluoride donor. This method is capable of rapidly producing linear alpha(1 -> 6) oligomannan thioglycosides in a convenient and cost-effective manner without the need of column purification after each glycosylation step.

  DOI：

  10.1021/ol702743x

文献信息

• Imidazolium Cation Supported Solution-Phase Assembly of Homolinear α(1→6)−Linked Octamannoside: An Efficient Alternate Approach for Oligosaccharide Synthesis
  作者：Charu K. Yerneni、Vibha Pathak、Ashish K. Pathak

  DOI：10.1021/jo901169u

  日期：2009.8.21

  An efficient, simple convergent assembly of a homolinear alpha(1 -> 6)-linked octamannosyl thioglycoside was obtained starting from imidazolium cation-tagged mannosyl fluoride and thiomannoside using block couplings. During chain elongation glycosylation reactions no column chromatographic purifications were used.