allyl 6-O-benzyl-2-deoxy-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside | 1333477-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: allyl 6-O-benzyl-2-deoxy-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
• 英文别名: 9H-fluoren-9-ylmethyl [(2R,3S,4R,5R,6S)-3-hydroxy-2-(phenylmethoxymethyl)-6-prop-2-enoxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] carbonate
• CAS: 1333477-11-4
• 化学式: C₃₄H₃₄Cl₃NO₉
• 分子量: 707.004
• InChiKey: CRBFBZWUXIILAG-CWMPKMHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  9

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside	183388-21-8	C19H22Cl3NO7	482.745

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	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	C45H43Cl3NO12P	927.169

反应信息

• 作为反应物：
  描述：

  allyl 6-O-benzyl-2-deoxy-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 、 二苯基N,N'-二异丙基亚磷酰胺 在 5-苯基四氮唑 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以98%的产率得到allyl 6-O-benzyl-2-deoxy-4-O-(di-O-benzylphosphono)-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
  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：

  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 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 allyl 6-O-benzyl-2-deoxy-3-O-(9-fluorenylmethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
  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.