2-(trimethylsilyl)ethyl (3-S-acetyl-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside | 678995-67-0

• 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 (3-S-acetyl-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
• CAS: 678995-67-0
• 化学式: C₅₄H₅₆O₁₅SSi
• 分子量: 1005.18
• InChiKey: JSHLGWWEPMCZAS-PHYKAPBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.47
• 重原子数：
  71.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  177.65
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl (3-S-acetyl-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 乙酸肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (2R,3R,4S,5R,6R)-5-(((2S,4aR,6S,7S,8S,8aS)-7-(benzoyloxy)-8-mercapto-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-6-((benzoyloxy)methyl)-2-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4-diyl dibenzoate
  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-3-O-(4-methoxybenzyl)-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 吡啶 、 ammonium cerium(IV) nitrate 、 四丁基亚硝酸铵 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 18.34h， 生成 2-(trimethylsilyl)ethyl (3-S-acetyl-2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-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