2-(trimethylsilyl)ethyl (2,3-di-O-acetyl-6-O-trifluoromethanesulfonyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 678995-56-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(trimethylsilyl)ethyl (2,3-di-O-acetyl-6-O-trifluoromethanesulfonyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 678995-56-7
• 化学式: C₂₈H₄₃F₃O₁₈SSi
• 分子量: 784.785
• InChiKey: PAUHYEADZZMZCS-FDXOKOSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  51.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  232.02
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  2-Thiosialic acid methyl ester peracetate 、 2-(trimethylsilyl)ethyl (2,3-di-O-acetyl-6-O-trifluoromethanesulfonyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以0.301 g的产率得到2-(trimethylsilyl)ethyl S-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2-6)-(2,3-di-O-acetyl-6-thio-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  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 (2,3-di-O-acetyl-4,6-benzylidene-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 2-(trimethylsilyl)ethyl (2,3-di-O-acetyl-6-O-trifluoromethanesulfonyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  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