2-naphthyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside | 1069074-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-naphthyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
• CAS: 1069074-13-0
• 化学式: C₃₉H₃₈O₆S
• 分子量: 634.793
• InChiKey: KNACPLQECPMJGW-WEMFOFRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.98
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-naphthyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 在 samarium diiodide 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 3,4,6-三苄氧基-D-葡萄烯糖
  参考文献：
  名称：

  1,2-cis-C-glycoside synthesis by samarium diiodide-promoted radical cyclizations

  摘要：

  AbstractThe samarium diiodide reduction of glycosyl pyridyl sulfones bearing a silicon‐tethered unsaturated group at the C2–OH position leads to the stereo‐specific synthesis of 1,2‐cis‐C‐glycosides in good yield after desilylation. These reactions proceed via an anomeric radical with subsequent 5‐exo cyclization. Unlike the corresponding glycosyl phenyl sulfones, the pyridyl derivatives react instantaneously with samarium diiodide and do not require a cosolvent such as hexamethylphosphoramide (HMPA). Under these reaction conditions radical cyclization precedes the second reduction step. Examples of 5‐exo‐trig and ‐dig ring closures are given. The synthetic utility of this method was demonstrated by a short synthesis of methyl C‐isomaltoside.

  DOI：

  10.1002/chem.19970030822
• 作为产物：
  描述：

  3,4,6-三-O-苄基-beta-D-吡喃甘露糖-1,2-(甲基原乙酸酯) 、 2-萘硫醇 在 mercury dibromide 作用下， 以 乙腈 为溶剂， 反应 27.0h， 以69%的产率得到2-naphthyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Biotin Sulfone as a New Tool for Synthetic Oligosaccharide Immobilization: Application to Multiple Analysis Profiling and Surface Plasmonic Analysis of Anti-Candida albicans Antibody Reactivity against α and β (1→2) Oligomannosides

  摘要：

  As a part of our glycoantigen synthetic program for diagnosis and basic analysis of yeast-related pathogenic mechanisms, a library of 1-->2 oligomannosides suitable for immunoanalysis was prepared. The use of biotin sulfone, an oxidized form of biotin, offers a convenient solution for both oligosaccharide synthesis and immobilization on microspheres and surface plasmon resonance sensors. The application of this new strategy for the analysis of anti-Candida albicans antibody response through multiple-analyte profiling technology (Luminex) and with surface plasmonic analysis using biotin tagged synthetic oligosaccharides on avidin coated surfaces was validated using monoclonal antibodies.

  DOI：

  10.1021/jm800099g