(3R,4S,5R,6R)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)oxy)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trifluoro-N-phenylacetimidate | 1352618-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (3R,4S,5R,6R)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)oxy)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trifluoro-N-phenylacetimidate
• CAS: 1352618-51-9
• 化学式: C₅₀H₄₄F₃NO₈
• 分子量: 843.896
• InChiKey: OFCLULMTPWBIPQ-VEWVWOIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.74
• 重原子数：
  62.0
• 可旋转键数：
  15.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  94.04
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R,6R)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)oxy)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trifluoro-N-phenylacetimidate 、 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以83%的产率得到
  参考文献：
  名称：

  A Possible Oligosaccharide-Conjugate Vaccine Candidate for Clostridium difficile Is Antigenic and Immunogenic

  摘要：

  Nosocomial infections with the Gram-positive pathogen Clostridium difficile pose a major risk for hospitalized patients and result in significant costs to health care systems. Here, we present the chemical synthesis of a PS-II hapten of a cell wall polysaccharide of hypervirulent ribotype 027 of C. difficile. Mice were immunized with a conjugate consisting of the synthetic hexasaccharide and the diphtheria toxoid variant CRM197. The immunogenicity of the glycan repeating unit was demonstrated by the presence of specific IgG antibodies in the serum of immunized mice. Murine monoclonal antibodies interact with the synthetic hexasaccharide, as determined by microarray analysis. Finally, we found that specific IgA antibodies in the stool of hospital patients infected with C. difficile recognize the synthetic PS-II hexasaccharide hapten.

  DOI：

  10.1016/j.chembiol.2011.03.009
• 作为产物：
  描述：

  ethyl 2,3,6-tri-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-glucopyranoside 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 caesium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (3R,4S,5R,6R)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)oxy)-3,4-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl 2,2,2-trifluoro-N-phenylacetimidate
  参考文献：
  名称：

  A Possible Oligosaccharide-Conjugate Vaccine Candidate for Clostridium difficile Is Antigenic and Immunogenic

  摘要：

  Nosocomial infections with the Gram-positive pathogen Clostridium difficile pose a major risk for hospitalized patients and result in significant costs to health care systems. Here, we present the chemical synthesis of a PS-II hapten of a cell wall polysaccharide of hypervirulent ribotype 027 of C. difficile. Mice were immunized with a conjugate consisting of the synthetic hexasaccharide and the diphtheria toxoid variant CRM197. The immunogenicity of the glycan repeating unit was demonstrated by the presence of specific IgG antibodies in the serum of immunized mice. Murine monoclonal antibodies interact with the synthetic hexasaccharide, as determined by microarray analysis. Finally, we found that specific IgA antibodies in the stool of hospital patients infected with C. difficile recognize the synthetic PS-II hexasaccharide hapten.

  DOI：

  10.1016/j.chembiol.2011.03.009