5-methoxycarbonylpentyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside | 1069074-26-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-methoxycarbonylpentyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: methyl 6-[(2S,3S,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyhexanoate
• CAS: 1069074-26-5
• 化学式: C₃₄H₄₂O₈
• 分子量: 578.703
• InChiKey: IMRLDGMWNZGPOK-FJWBHYDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-methoxycarbonylpentyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 、 (2-methyl-5-tert-butylphenyl) 2-O-benzoyl-3-O-levulinoyl-4,6-di-O-benzyl-1-thio-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 0.75h， 以78%的产率得到5-methoxycarbonylpentyl 2-O-(2-O-benzoyl-3-O-levulinoyl-4,6-di-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Biotin sulfone tagged oligomannosides as immunogens for eliciting antibodies against specific mannan epitopes

  摘要：

  Biotinylated tri and tetrasaccharide: alpha Man (1 -> 3) alpha Man (1 -> 2) alpha Man; alpha Man (1 -> 3) alpha Man (1 -> 2) alpha Man (1 -> 2) alpha Man were prepared using methyl tertbutyl phenyl thioglycosides glycosyl donors (MBP) and biotin sulfone strategy. Three key mannosyl thioglycosidic donors have been prepared: one for 1 -> 2 linkage and two for the 1 -> 3 linkage (protected with a 4,6-O-benzylidene or a 4,6-di-O-benzyl). The benzyliden protected one was not found reactive enough, and the benzylated donor was preferred. These biotinylated oligomanosides were evaluated as antigen in Crohn disease diagnosis and used coupled to streptavidin as hapten for eliciting polyclonal antibodies in mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.048
• 作为产物：
  描述：

  甲醇 、 5-ethoxycarbonylpentyl 2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 sodium 作用下， 反应 4.0h， 以89%的产率得到5-methoxycarbonylpentyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Biotin sulfone tagged oligomannosides as immunogens for eliciting antibodies against specific mannan epitopes

  摘要：

  Biotinylated tri and tetrasaccharide: alpha Man (1 -> 3) alpha Man (1 -> 2) alpha Man; alpha Man (1 -> 3) alpha Man (1 -> 2) alpha Man (1 -> 2) alpha Man were prepared using methyl tertbutyl phenyl thioglycosides glycosyl donors (MBP) and biotin sulfone strategy. Three key mannosyl thioglycosidic donors have been prepared: one for 1 -> 2 linkage and two for the 1 -> 3 linkage (protected with a 4,6-O-benzylidene or a 4,6-di-O-benzyl). The benzyliden protected one was not found reactive enough, and the benzylated donor was preferred. These biotinylated oligomanosides were evaluated as antigen in Crohn disease diagnosis and used coupled to streptavidin as hapten for eliciting polyclonal antibodies in mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.048

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.
• Biotin sulfone tagged oligomannosides as immunogens for eliciting antibodies against specific mannan epitopes
  作者：Guillaume Despras、Raymond Robert、Boualem Sendid、Emeline Machez、Daniel Poulain、Jean-Maurice Mallet

  DOI：10.1016/j.bmc.2011.12.048

  日期：2012.3

  Biotinylated tri and tetrasaccharide: alpha Man (1 -> 3) alpha Man (1 -> 2) alpha Man; alpha Man (1 -> 3) alpha Man (1 -> 2) alpha Man (1 -> 2) alpha Man were prepared using methyl tertbutyl phenyl thioglycosides glycosyl donors (MBP) and biotin sulfone strategy. Three key mannosyl thioglycosidic donors have been prepared: one for 1 -> 2 linkage and two for the 1 -> 3 linkage (protected with a 4,6-O-benzylidene or a 4,6-di-O-benzyl). The benzyliden protected one was not found reactive enough, and the benzylated donor was preferred. These biotinylated oligomanosides were evaluated as antigen in Crohn disease diagnosis and used coupled to streptavidin as hapten for eliciting polyclonal antibodies in mice. (C) 2011 Elsevier Ltd. All rights reserved.