O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl dibenzylphosphate | 1527527-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl dibenzylphosphate
• CAS: 1527527-32-7
• 化学式: C₁₀₁H₁₀₁O₂₄P
• 分子量: 1729.87
• InChiKey: ARKJONXACLTBIC-UWLPSDKKSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl dibenzylphosphate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、200.0 kPa 条件下， 以67%的产率得到O-(β-D-mannopyranosyl)-(1→2)-O-(β-D-mannopyranosyl)-(1→2)-O-(β-D-mannopyranosyl)-(1→2)-α-D-mannopyranosylphosphate
  参考文献：
  名称：

  Synthesis and conformational analysis of phosphorylated β-(1→2) linked mannosides

  摘要：

  Phosphorylated beta-(1 -> 2)-oligomannosides are found on the cell surface of several Candida species, including Candida albicans (an opportunistic pathogen). These molecules are believed to take part in the invasion process of fungal infections, which in the case of C. albicans can lead to severe bloodstream infections and death, and can therefore be considered important from a biological standpoint. Understanding the mechanism of their action requires access to the corresponding oligosaccharide model compounds in pure form. In the present work, synthesis of the model core structures involved in the invasion process of C. albicans, consisting of phosphorylated beta-(1 -> 2)-linked mannotriose and tetraose, is reported. In order to elucidate the nature of these molecules in more detail, an extensive NMR-spectroscopic study encompassing complete spectral characterization, conformational analysis and molecular modelling was performed. The obtained results were also compared to similar chemical entities devoid of the charged phosphate group. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.10.017
• 作为产物：
  描述：

  O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-3-O-benzyl-4,6-O-benzylidene-D-mannopyranose 、 二苯基N,N'-二异丙基亚磷酰胺 在 四氮唑 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1→2)-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl dibenzylphosphate
  参考文献：
  名称：

  Synthesis and conformational analysis of phosphorylated β-(1→2) linked mannosides

  摘要：

  Phosphorylated beta-(1 -> 2)-oligomannosides are found on the cell surface of several Candida species, including Candida albicans (an opportunistic pathogen). These molecules are believed to take part in the invasion process of fungal infections, which in the case of C. albicans can lead to severe bloodstream infections and death, and can therefore be considered important from a biological standpoint. Understanding the mechanism of their action requires access to the corresponding oligosaccharide model compounds in pure form. In the present work, synthesis of the model core structures involved in the invasion process of C. albicans, consisting of phosphorylated beta-(1 -> 2)-linked mannotriose and tetraose, is reported. In order to elucidate the nature of these molecules in more detail, an extensive NMR-spectroscopic study encompassing complete spectral characterization, conformational analysis and molecular modelling was performed. The obtained results were also compared to similar chemical entities devoid of the charged phosphate group. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.10.017