6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranose | 1333477-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranose
• 英文别名: 9H-fluoren-9-ylmethyl [(2S,3R,4R,5S,6R)-2-hydroxy-5-[oxido-bis(phenylmethoxy)phosphaniumyl]oxy-6-(phenylmethoxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] carbonate
• CAS: 1333477-13-6
• 化学式: C₄₅H₄₃Cl₃NO₁₂P
• 分子量: 927.169
• InChiKey: ZTNCKWXIBBZNBL-MHBOMZLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  62
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  163
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 5-苯基四氮唑 、 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 氢气 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose 、 6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranose
  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

文献信息

• Synthesis of a dimeric monosaccharide lipid A mimic and its synergistic effect on the immunostimulatory activity of lipopolysaccharide
  作者：Jordan D. Lewicky、Marina Ulanova、Zi-Hua Jiang

  DOI：10.1016/j.carres.2011.05.018

  日期：2011.9

  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.