benzyl [N-benzyloxycarbonyl-3-amino-propyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-octulopyranosid] onate | 1392224-71-3

• 分子结构分类: 有机化合物
• 英文名称: benzyl [N-benzyloxycarbonyl-3-amino-propyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-octulopyranosid] onate
• CAS: 1392224-71-3
• 化学式: C₃₆H₄₃NO₁₀
• 分子量: 649.738
• InChiKey: LBIBKSBPXRZNIY-MWRIEZPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  131.01
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  benzyl [N-benzyloxycarbonyl-3-amino-propyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-octulopyranosid] onate 、 3-O-acetyl-2-deoxy-2-(2,2,2-trichloroethyloxycarbonyl)-amino-4,6-O-(di-tert-butylsilanediyl)-α-D-galactosamine-(1→2)-4,6-di-O-benzylidene-3-O-(2-methylnaphthyl)-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-O-levulinoyl-α-D-mannopyranosyl trichloroacetimidate 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到benzyl 3-O-acetyl-2-deoxy-2-(2,2,2-trichloroethyloxycarbonyl)-amino-4,6-O-(di-tert-butylsilanediyl)-α-D-galactosamine-(1→2)-4,6-di-O-benzylidene-3-O-(2-methylnaphthyl)-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-O-levulinoyl-α-D-mannopyranosyl-(1→5)-[N-benzyloxycarbonyl-3-amino-propyl-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-mannooctulopyranosid]onate
  参考文献：
  名称：

  Chemical Synthesis and Immunological Evaluation of the Inner Core Oligosaccharide of Francisella tularensis

  摘要：

  Francisella tularensis, which is a Gram negative bacterium that causes tularemia, has been classified by the Center for Disease Control and Prevention (CDC) as a category A bioweapon. The development of vaccines, immunotherapeutics, and diagnostics for F. tularensis requires a detailed knowledge of the saccharide structures that can be recognized by protective antibodies. We have synthesized the inner core region of the lipopolysaccharide (LPS) of F. tularensis to probe antigenic responses elicited by a live and subunit vaccine. The successful preparation of the target compound relied on the use of a disaccharide which was modified by the orthogonal protecting groups diethylisopropylsilyl (DEIPS), 2-naphthylmethyl (Nap), allyl ether (All), and levulinoyl (Lev) ester. The ability to remove the protecting groups in different orders made it possible to establish the optimal glycosylations sequence to prepare a highly crowded 1,2,3-cis configured branching point. A variety of different methods were exploited to control anomeric selectivities of the glycosylations. A comparison of the H-1 NMR spectra of isolated material and the synthetic derivative confirmed the reported structural assignment of the inner core oligosaccharide of F. tularensis. The observation that immunizations with LPS lead to antibody responses to the inner core saccharides provides an impetus to further explore this compound as a vaccine candidate.

  DOI：

  10.1021/ja306274v
• 作为产物：
  描述：

  2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol 在 甲醇 、 六甲基磷酰三胺 、 ruthenium trichloride 、 sodium periodate 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 二乙胺基三氟化硫 、 三氟化硼乙醚 、 水 、 二正丁基氧化锡 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 38.92h， 生成 benzyl [N-benzyloxycarbonyl-3-amino-propyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-octulopyranosid] onate
  参考文献：
  名称：

  Chemical Synthesis and Immunological Evaluation of the Inner Core Oligosaccharide of Francisella tularensis

  摘要：

  Francisella tularensis, which is a Gram negative bacterium that causes tularemia, has been classified by the Center for Disease Control and Prevention (CDC) as a category A bioweapon. The development of vaccines, immunotherapeutics, and diagnostics for F. tularensis requires a detailed knowledge of the saccharide structures that can be recognized by protective antibodies. We have synthesized the inner core region of the lipopolysaccharide (LPS) of F. tularensis to probe antigenic responses elicited by a live and subunit vaccine. The successful preparation of the target compound relied on the use of a disaccharide which was modified by the orthogonal protecting groups diethylisopropylsilyl (DEIPS), 2-naphthylmethyl (Nap), allyl ether (All), and levulinoyl (Lev) ester. The ability to remove the protecting groups in different orders made it possible to establish the optimal glycosylations sequence to prepare a highly crowded 1,2,3-cis configured branching point. A variety of different methods were exploited to control anomeric selectivities of the glycosylations. A comparison of the H-1 NMR spectra of isolated material and the synthetic derivative confirmed the reported structural assignment of the inner core oligosaccharide of F. tularensis. The observation that immunizations with LPS lead to antibody responses to the inner core saccharides provides an impetus to further explore this compound as a vaccine candidate.

  DOI：

  10.1021/ja306274v