| 678995-58-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• CAS: 678995-58-9
• 化学式: C₅₆H₇₂N₄O₃₀S
• 分子量: 1313.26
• InChiKey: SIMIHNZUDIIOED-KYIWSGBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  91.0
• 可旋转键数：
  29.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  439.61
• 氢给体数：
  1.0
• 氢受体数：
  32.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 水 、 三苯基膦 作用下， 反应 4.0h， 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：

  methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-hydroxyoxan-3-yl]oxyoxan-2-yl]methylsulfanyl]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 在 calcium sulfate 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 7.33h， 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