phenyl 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)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside | 1527527-16-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 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)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• CAS: 1527527-16-7
• 化学式: C₇₃H₇₂O₁₅S
• 分子量: 1221.43
• InChiKey: JXAPXORHISTNJA-INUMKFMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.41
• 重原子数：
  89.0
• 可旋转键数：
  21.0
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  138.45
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  phenyl 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)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 丙酮 为溶剂， 反应 1.5h， 以28%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-dDmannopyranosyl)-(1→2)-3-O-benzyl-4,6-O-benzylidene-D-mannopyranose
  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：

  phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1->2)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 、 (2R,4AR,6R,7S,8R,8AR)-8-(苄氧基)-2-苯基-6-(苯硫基)六氢吡喃并[3,2-D][1,3]二氧杂环己烯-7-醇 在 三氟甲磺酸酐 、 BSP 、 2,4,6-三叔丁基嘧啶 、 辛烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.75h， 以62%的产率得到phenyl 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)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
  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