1-[6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethan-2-ol | 1333477-15-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethan-2-ol
• CAS: 1333477-15-8
• 化学式: C₄₇H₄₇Cl₃NO₁₃P
• 分子量: 971.222
• InChiKey: LZCRUHYWLYKFSW-HQZUZMDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.66
• 重原子数：
  65.0
• 可旋转键数：
  20.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  166.54
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  1-[6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethan-2-ol 、 6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到1,2 di-[6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-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：

  6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 1-[6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyloxy]ethan-2-ol
  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