5-methoxycarbonylpentyl 2-O-(2-O-benzoyl-3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-4,6-di-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside | 1361016-68-3

• 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-benzoyl-3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-4,6-di-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• CAS: 1361016-68-3
• 化学式: C₉₅H₁₀₀O₂₀
• 分子量: 1561.83
• InChiKey: RCESLHZQRUJMMK-PNGLOKKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.71
• 重原子数：
  115.0
• 可旋转键数：
  42.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  208.12
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  5-methoxycarbonylpentyl 2-O-(2-O-benzoyl-3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-4,6-di-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 甲醇 、 sodium 作用下， 反应 4.0h， 以75%的产率得到5-methoxycarbonylpentyl 2-O-(3-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-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：

  (2-methyl-5-tert-butylphenyl) 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-D-mannopyranoside 、 5-methoxycarbonylpentyl 2-O-(2-O-benzoyl-4,6-di-O-benzyl-α-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 0.75h， 以80%的产率得到5-methoxycarbonylpentyl 2-O-(2-O-benzoyl-3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-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