1,4-bis((3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1<*>3)-2,6-di-O-acetyl-β-D-galactopyranosyl)oxy)butane | 163965-04-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-bis((3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1<*>3)-2,6-di-O-acetyl-β-D-galactopyranosyl)oxy)butane
• 英文别名: 1,4-bis([3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1[*]3)-2,6-di-O-acetyl-β-D-galactopyranosyl]oxy)butane
• CAS: 163965-04-6
• 化学式: C₆₄H₇₆N₂O₃₄
• 分子量: 1417.3
• InChiKey: NJCIRSZTPVJDFD-RJRSBTOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.64
• 重原子数：
  100.0
• 可旋转键数：
  27.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  452.06
• 氢给体数：
  2.0
• 氢受体数：
  34.0

反应信息

• 作为反应物：
  描述：

  1,4-bis((3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1<*>3)-2,6-di-O-acetyl-β-D-galactopyranosyl)oxy)butane 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Ligand Recognition by E-Selectin: Synthesis, Inhibitory Activity and Conformational Analysis of Bivalent Sialyl Lewis x Analogs

  摘要：

  Several sialyl Lewis x dimers anchored onto a galactose template or attached to 1,4-butanediol or 1,5-pentanediol have been prepared chemoenzymatically and evaluated as inhibitors of E-selectin-mediated cell adhesion. Two monosaccharide units were simultaneously incorporated (i.e., Gal, NeuAc, Fuc) by a glycosyltransferase into a chemically synthesized core structure containing GlcNAc and Gal. Each of the galactose-anchored dimers had higher activity than the sialyl Lewis x pentasaccharide la, with the general trend being 3,6-linked > 2,3 greater than or equal to 4,6 greater than or equal to 2,6 monomer. The dimers linked to butanediol or pentanediol showed the same level of activity as the pentasaccharide monomer. Conformational analysis of these dimers with NMR indicated that each sialyl Lewis x domain of the dimers retains the same conformation as the monomer. The differences in activity of the dimers most likely derive from differences in the relative orientation and distance between the monomer domains, suggesting the importance of the linker used in the preparation of dimers.

  DOI：

  10.1021/ja00106a008
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide 、 1,4-bis((2,6-di-O-acetyl-β-D-galactopyranosyl)oxy)butane 在 2,3,5-三甲基吡啶 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 生成 1,4-bis((3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1<*>3)-2,6-di-O-acetyl-β-D-galactopyranosyl)oxy)butane
  参考文献：
  名称：

  Ligand Recognition by E-Selectin: Synthesis, Inhibitory Activity and Conformational Analysis of Bivalent Sialyl Lewis x Analogs

  摘要：

  Several sialyl Lewis x dimers anchored onto a galactose template or attached to 1,4-butanediol or 1,5-pentanediol have been prepared chemoenzymatically and evaluated as inhibitors of E-selectin-mediated cell adhesion. Two monosaccharide units were simultaneously incorporated (i.e., Gal, NeuAc, Fuc) by a glycosyltransferase into a chemically synthesized core structure containing GlcNAc and Gal. Each of the galactose-anchored dimers had higher activity than the sialyl Lewis x pentasaccharide la, with the general trend being 3,6-linked > 2,3 greater than or equal to 4,6 greater than or equal to 2,6 monomer. The dimers linked to butanediol or pentanediol showed the same level of activity as the pentasaccharide monomer. Conformational analysis of these dimers with NMR indicated that each sialyl Lewis x domain of the dimers retains the same conformation as the monomer. The differences in activity of the dimers most likely derive from differences in the relative orientation and distance between the monomer domains, suggesting the importance of the linker used in the preparation of dimers.

  DOI：

  10.1021/ja00106a008