p-[2-(benzyloxycarbonyl)ethyl]phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside | 359686-41-2

• 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: p-[2-(benzyloxycarbonyl)ethyl]phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• 英文别名: benzyl 3-[4-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphenyl]propanoate
• CAS: 359686-41-2
• 化学式: C₃₀H₃₄O₁₂
• 分子量: 586.593
• InChiKey: QJQXXRMIDIFKIA-AARHSHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  p-[2-(benzyloxycarbonyl)ethyl]phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 palladium dihydroxide 吡啶 、 18-冠醚-6 、 氢气 、 苯甲醇钠 、 三丁基氧化锡 作用下， 以 乙醇 、 甲苯 、 苯甲醇 、 苯 为溶剂， 反应 94.0h， 生成 p-(2-carboxyethyl)phenyl 4-O-acetyl-2-deoxy-2-fluoro-3,6-di-O-pivaloyl-β-D-mannopyranoside
  参考文献：
  名称：

  SYNTHESIS OF NEW GLYCOPOLYMERS CONTAINING β-D-MANNOPYRANOSE, ANDC-2-SUBSTITUTED β-D-MANNOPYRANOSE RESIDUES AS A NEW CLASS OF INHIBITOR

  摘要：

  New styryl monomers containing beta -D-mannopyranose, 2-acetamido-2-deoxy-beta -D-mannopyranose, 2-deoxy-2-fluoro-beta -D-mannopyranose, and 2-deoxy-beta -D-arabino-hexopyranose on their side chains, were efficiently synthesized as a new class of a potent inhibitor resistant to exo-or-mannosidase digestion. The binding affinity of the carbohydrate polymers obtained from those mannopyranosyl styryl monomers by radical polymerization with Concanavalin A were evaluated. A binding assay indicated that the multivalency effect and the affinity enhancement attained by modification at the C-2 position of the beta -D-mannopyranoside residue resulted in the beta -D-mannopyranosyl polymer which has the same affinity as that of the alpha -D-mannopyranosyl polymer.

  DOI：

  10.1081/car-100103953
• 作为产物：
  描述：

  苄基3-(4-羟基苯基)丙酸酯 、 beta-D-半乳糖五乙酸酯 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以59%的产率得到p-[2-(benzyloxycarbonyl)ethyl]phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  SYNTHESIS OF NEW GLYCOPOLYMERS CONTAINING β-D-MANNOPYRANOSE, ANDC-2-SUBSTITUTED β-D-MANNOPYRANOSE RESIDUES AS A NEW CLASS OF INHIBITOR

  摘要：

  New styryl monomers containing beta -D-mannopyranose, 2-acetamido-2-deoxy-beta -D-mannopyranose, 2-deoxy-2-fluoro-beta -D-mannopyranose, and 2-deoxy-beta -D-arabino-hexopyranose on their side chains, were efficiently synthesized as a new class of a potent inhibitor resistant to exo-or-mannosidase digestion. The binding affinity of the carbohydrate polymers obtained from those mannopyranosyl styryl monomers by radical polymerization with Concanavalin A were evaluated. A binding assay indicated that the multivalency effect and the affinity enhancement attained by modification at the C-2 position of the beta -D-mannopyranoside residue resulted in the beta -D-mannopyranosyl polymer which has the same affinity as that of the alpha -D-mannopyranosyl polymer.

  DOI：

  10.1081/car-100103953