2-(trimethylsilyl)ethyl 2-O-benzoyl-4,6-O-benzylidene-β-D-gulopyranoside | 678995-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-(trimethylsilyl)ethyl 2-O-benzoyl-4,6-O-benzylidene-β-D-gulopyranoside
• 英文别名: 2-(trimethylsilyl)ethyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside
• CAS: 678995-60-3
• 化学式: C₂₅H₃₂O₇Si
• 分子量: 472.61
• InChiKey: ZQONZVRJJGYZKO-REYDMIKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2-O-benzoyl-4,6-O-benzylidene-β-D-gulopyranoside 在 吡啶 、 air 、 乙酸肼 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.33h， 生成
  参考文献：
  名称：

  S-Linked Ganglioside Analogues for Use in Conjugate Vaccines

  摘要：

  Glycosidase resistant thioglycoside precursors of the melanoma-associated ganglioside GM(2) have been synthesized starting from lactose. Syntheses of several analogues of ganglioside GM(3) and a positional isomer have been developed. These compounds contain thio-linked sialic acid residues and a modified ceramide aglycon functionalized for coupling to proteins, surfaces, or matrices. The hydrolytic stability of these oligosaccharides enhances the immunogenicity of the corresponding conjugate vaccines by ensuring their integrity in the acidic compartments of antigen processing cells.

  DOI：

  10.1021/ol036460p
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside 在 吡啶 、 四丁基亚硝酸铵 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.5h， 生成 2-(trimethylsilyl)ethyl 2-O-benzoyl-4,6-O-benzylidene-β-D-gulopyranoside
  参考文献：
  名称：

  S-Linked Ganglioside Analogues for Use in Conjugate Vaccines

  摘要：

  Glycosidase resistant thioglycoside precursors of the melanoma-associated ganglioside GM(2) have been synthesized starting from lactose. Syntheses of several analogues of ganglioside GM(3) and a positional isomer have been developed. These compounds contain thio-linked sialic acid residues and a modified ceramide aglycon functionalized for coupling to proteins, surfaces, or matrices. The hydrolytic stability of these oligosaccharides enhances the immunogenicity of the corresponding conjugate vaccines by ensuring their integrity in the acidic compartments of antigen processing cells.

  DOI：

  10.1021/ol036460p

文献信息

• Design and Synthesis of a Novel Ganglioside Ligand for Influenza A Viruses †
  作者：Tomohiro Nohara、Akihiro Imamura、Maho Yamaguchi、Kazuya I. P. J. Hidari、Takashi Suzuki、Tatsuya Komori、Hiromune Ando、Hideharu Ishida、Makoto Kiso

  DOI：10.3390/molecules17089590

  日期：——

  A novel ganglioside bearing Neua2-3Gal and Neua2-6Gal structures as distal sequences was designed as a ligand for influenza A viruses. The efficient synthesis of the designed ganglioside was accomplished by employing the cassette coupling approach as a key reaction, which was executed between the non-reducing end of the oligosaccharide and the cyclic glucosylceramide moiety. Examination of its binding activity to influenza A viruses revealed that the new ligand is recognized by Neua2-3 and 2-6 type viruses.

  设计了一种新型神经节苷脂，其远端序列包含NeuA2-3Gal和NeuA2-6Gal结构，作为流感A病毒的配体。通过采用盒式偶联法作为关键反应，实现了该设计神经节苷脂的高效合成，该反应在低聚糖的非还原端与环状葡萄糖基神经酰胺之间进行。检测其与流感A病毒的结合活性发现，新型配体被NeuA2-3型和2-6型病毒所识别。