2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-acetyl-D-galactopyranose | 629624-93-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-acetyl-D-galactopyranose
• 英文别名: Gal2Ac3Ac4Ac6Ac(b1-4)Glc2Ac3Ac6Ac(b1-6)Gal1Ac2Ac3Ac4Ac；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-[[(2R,3S,4S,5R)-3,4,5,6-tetraacetyloxyoxan-2-yl]methoxy]-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 629624-93-7
• 化学式: C₄₀H₅₄O₂₇
• 分子量: 966.853
• InChiKey: OSTFFOHATSTXHD-GQYQXCDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  67
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  335
• 氢给体数：
  0
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-acetyl-D-galactopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以74%的产率得到β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-D-galactopyranose
  参考文献：
  名称：

  Chemically Defined Sialoside Scaffolds for Investigation of Multivalent Interactions with Sialic Acid Binding Proteins^†

  摘要：

  Four glycodendrons and a glycocluster were synthesized fromcarbohydrate building blocks to form paucivalent (di- to tetravalent) structures of controlled scaffold architectures. Enzymatic sialylation of the functionalized cluster and dendrons, terminated in lactose residues, generated a library of paucivalent synthetic sialosides displaying sialic acids with different dispositions. These newly constructed bioactive sialic acid-based structures were differentially recognized by sialoadhesin, a mammalian macrophage sialic acid binding protein. The binding of the sialosides to sialoadhesin was evaluated by an enzyme-linked immunosorbant assay to investigate the complementarity of scaffold structure and binding to sialoadhesin. Modulating the interaction between sialoadhesin and its sialic acid ligands has important implications in immunobiology.

  DOI：

  10.1021/jo030203g
• 作为产物：
  描述：

  乙酸酐 、 β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-D-galactopyranose 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 16.0h， 以15.15 g的产率得到2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-acetyl-D-galactopyranose
  参考文献：
  名称：

  Chemically Defined Sialoside Scaffolds for Investigation of Multivalent Interactions with Sialic Acid Binding Proteins^†

  摘要：

  Four glycodendrons and a glycocluster were synthesized fromcarbohydrate building blocks to form paucivalent (di- to tetravalent) structures of controlled scaffold architectures. Enzymatic sialylation of the functionalized cluster and dendrons, terminated in lactose residues, generated a library of paucivalent synthetic sialosides displaying sialic acids with different dispositions. These newly constructed bioactive sialic acid-based structures were differentially recognized by sialoadhesin, a mammalian macrophage sialic acid binding protein. The binding of the sialosides to sialoadhesin was evaluated by an enzyme-linked immunosorbant assay to investigate the complementarity of scaffold structure and binding to sialoadhesin. Modulating the interaction between sialoadhesin and its sialic acid ligands has important implications in immunobiology.

  DOI：

  10.1021/jo030203g