1,2 di-[6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-((R)-3-tetradecanoyloxytetradecanamido)-β-D-glucopyranosyloxy]ethane | 1333477-22-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2 di-[6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-((R)-3-tetradecanoyloxytetradecanamido)-β-D-glucopyranosyloxy]ethane
• CAS: 1333477-22-7
• 化学式: C₁₄₂H₁₉₀N₂O₂₆P₂
• 分子量: 2403.02
• InChiKey: DTUFCVSGBHKGPH-XWXWNDNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  34.24
• 重原子数：
  172.0
• 可旋转键数：
  87.0
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  326.76
• 氢给体数：
  2.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  1,2 di-[6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-((R)-3-tetradecanoyloxytetradecanamido)-β-D-glucopyranosyloxy]ethane 在 5%-palladium/activated carbon 、 氢气 、 溶剂黄146 、 哌啶 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 以65%的产率得到1,2 di-[2-deoxy-4-O-(phosphono)-2-((R)-3-tetradecanoyloxytetradecanamido)-β-D-glucopyranosyloxy]ethane
  参考文献：
  名称：

  Synthesis of a dimeric monosaccharide lipid A mimic and its synergistic effect on the immunostimulatory activity of lipopolysaccharide

  摘要：

  Bacterial endotoxin lipopolysaccharide (LPS) is a potent immune stimulant, with the recognition of LPS and its active principal lipid A mediated by the Toll-like receptor 4 (TLR4)/MD-2 receptor complex. Due to the broad downstream implications of TLR4-mediated signalling, TLR4 ligands show great potential for immunotherapeutic manipulations. In this paper a dimeric monosaccharide lipid A mimic (3) has been designed as a potential TLR4 ligand. The chemical synthesis and the preliminary biological studies are described. Compound 3 shows a significant synergistic effect on LPS-induced ICAM-1 expression in human monocytic THP-1 cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.018
• 作为产物：
  描述：

  、 (R)-3-(dodecanoyloxy)tetradecanoic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以997 mg的产率得到1,2 di-[6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-((R)-3-tetradecanoyloxytetradecanamido)-β-D-glucopyranosyloxy]ethane
  参考文献：
  名称：

  Synthesis of a dimeric monosaccharide lipid A mimic and its synergistic effect on the immunostimulatory activity of lipopolysaccharide

  摘要：

  Bacterial endotoxin lipopolysaccharide (LPS) is a potent immune stimulant, with the recognition of LPS and its active principal lipid A mediated by the Toll-like receptor 4 (TLR4)/MD-2 receptor complex. Due to the broad downstream implications of TLR4-mediated signalling, TLR4 ligands show great potential for immunotherapeutic manipulations. In this paper a dimeric monosaccharide lipid A mimic (3) has been designed as a potential TLR4 ligand. The chemical synthesis and the preliminary biological studies are described. Compound 3 shows a significant synergistic effect on LPS-induced ICAM-1 expression in human monocytic THP-1 cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.018