5-methoxycarbonylpentyl 2-O-(2-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside | 1069074-46-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methoxycarbonylpentyl 2-O-(2-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: methyl 6-[(2S,3S,4S,5R,6R)-3-[(2S,3S,4S,5R,6R)-3-[(2S,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyhexanoate
• CAS: 1069074-46-9
• 化学式: C₈₈H₉₈O₁₈
• 分子量: 1443.74
• InChiKey: WWNWFCUFCYFYHK-MHFRHBPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  106
• 可旋转键数：
  42
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  185
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2-naphthyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 、 5-methoxycarbonylpentyl 2-O-(2-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以87%的产率得到5-methoxycarbonylpentyl 2-O-(2-O-(2-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-3,4,6-tri-O-benzyl-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
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 5-methoxycarbonylpentyl 2-O-(2-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-3,4,6-tri-O-benzyl-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

文献信息

• Biotin Sulfone as a New Tool for Synthetic Oligosaccharide Immobilization: Application to Multiple Analysis Profiling and Surface Plasmonic Analysis of Anti-<i>Candida albicans</i> Antibody Reactivity against α and β (1→2) Oligomannosides
  作者：Mayeul Collot、Boualem Sendid、Aurélie Fievez、Camille Savaux、Annie Standaert-Vitse、Marc Tabouret、Anne Sophie Drucbert、Pierre Marie Danzé、Daniel Poulain、Jean-Maurice Mallet

  DOI：10.1021/jm800099g

  日期：2008.10.9

  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.