methyl O-<2,3-di-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-4-deoxy-β-D-xylo-hexopyranosyl>-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside | 131291-25-3

• 分子结构分类: 有机化合物
• 英文名称: methyl O-<2,3-di-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-4-deoxy-β-D-xylo-hexopyranosyl>-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
• CAS: 131291-25-3
• 化学式: C₉₁H₈₄O₂₃Si
• 分子量: 1573.74
• InChiKey: IWBHWSLLVHXUJY-MFZHIAFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.61
• 重原子数：
  115.0
• 可旋转键数：
  28.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  275.01
• 氢给体数：
  0.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  methyl O-<2,3-di-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-4-deoxy-β-D-xylo-hexopyranosyl>-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 boron trifluoride methanol complex 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以99%的产率得到methyl O-(2,3-di-O-benzoyl-4-deoxy-β-D-xylo-hexopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of specifically deoxygenated ligands related to (1→6)-β-d-galacto-oligosaccharides, and studies on their binding to monoclonal antigalactan antibodies

  摘要：

  Synthetic deoxygenated derivatives of methyl beta-glycosides of (1----6)-beta-D-galacto-oligosaccharides were prepared, and their binding to antigalactan monoclonal antibodies X24 and J539 (Fab') was studied. The results suggest the involvement of an additional, critical hydrogen bond in the highest affinity subsite (A), which now appears to require two hydrogen bonds from the 2- and 3-hydroxyls of the galactosyl residue to the protein, and one from the protein to O-4 of that residue. The data obtained with a series of oligosaccharides deoxygenated at position 3(1), 3(2), 3(3), 4(1), 4(2), or 4(3) support the binding patterns and subsite-arrangement inferred previously from studies with large numbers of deoxyfluoro-substituted ligands and this family of antibodies.

  DOI：

  10.1016/0008-6215(90)84033-q
• 作为产物：
  描述：

  2,3-di-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-4-deoxy-α-D-xylo-hexopyranosyl chloride 、 methyl O-(2,3,4-tri-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 2,4,6-三甲基吡啶 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以93%的产率得到methyl O-<2,3-di-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-4-deoxy-β-D-xylo-hexopyranosyl>-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of specifically deoxygenated ligands related to (1→6)-β-d-galacto-oligosaccharides, and studies on their binding to monoclonal antigalactan antibodies

  摘要：

  Synthetic deoxygenated derivatives of methyl beta-glycosides of (1----6)-beta-D-galacto-oligosaccharides were prepared, and their binding to antigalactan monoclonal antibodies X24 and J539 (Fab') was studied. The results suggest the involvement of an additional, critical hydrogen bond in the highest affinity subsite (A), which now appears to require two hydrogen bonds from the 2- and 3-hydroxyls of the galactosyl residue to the protein, and one from the protein to O-4 of that residue. The data obtained with a series of oligosaccharides deoxygenated at position 3(1), 3(2), 3(3), 4(1), 4(2), or 4(3) support the binding patterns and subsite-arrangement inferred previously from studies with large numbers of deoxyfluoro-substituted ligands and this family of antibodies.

  DOI：

  10.1016/0008-6215(90)84033-q