phenyl 4,6-benzylidene-2-O-(diethylisopropylsilyl)-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside | 1250346-26-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4,6-benzylidene-2-O-(diethylisopropylsilyl)-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside
• CAS: 1250346-26-9
• 化学式: C₃₇H₄₄O₅SSi
• 分子量: 628.905
• InChiKey: PHQGUZLVLLVLAQ-BFFWXZMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.14
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-benzylidene-2-O-(diethylisopropylsilyl)-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside 在 4-硝基苯亚磺酰氯 、 2,6-二叔丁基-4-甲基吡啶 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 19.08h， 生成 allyl 4,6-di-O-benzylidene-3-O-(2-methylnaphthyl)-β-D-mannopyranosyl-(1-4)-3,6-di-O-benzyl-2-O-levulinoyl-α-D-mannopyranoside
  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：

  phenyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside 、 二乙基异丙基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以76%的产率得到phenyl 4,6-benzylidene-2-O-(diethylisopropylsilyl)-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  用于制备高度支化寡糖的多功能正交保护基团

  摘要：

  基于二乙基异丙基甲硅烷基 (DEIPS)、甲基萘基 (Nap)、烯丙基醚和乙酰丙酰基 (Lev) 酯的使用，开发了一组新的正交保护基团。保护基团非常适合制备高度支化的寡糖，其用途已通过 β- d -Man-(1→4)- d -Man 二糖的化学合成得到证明，该二糖经过适当保护以制备一系列土拉弗朗西斯菌脂多糖的不寻常核心区域的部分结构。

  DOI：

  10.1021/ol101951u