p-[2-(benzyloxycarbonyl)ethyl]phenyl 2,4-di-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside | 359686-64-9

• 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 2,4-di-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,5-diacetyloxy-4-(2,2-dimethylpropanoyloxy)-6-[4-(3-oxo-3-phenylmethoxypropyl)phenoxy]oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 359686-64-9
• 化学式: C₃₆H₄₆O₁₂
• 分子量: 670.754
• InChiKey: ARNAJMADFNJRBB-BGOZSPGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  48
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 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 2,4-di-O-acetyl-3,6-di-O-pivaloyl-β-D-mannopyranoside 在 palladium dihydroxide 氢气 、 sodium methylate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 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 在 吡啶 、 18-冠醚-6 、 四氯化锡 、 苯甲醇钠 、 三丁基氧化锡 作用下， 以 二氯甲烷 、 甲苯 、 苯甲醇 、 苯 为溶剂， 反应 92.0h， 生成 p-[2-(benzyloxycarbonyl)ethyl]phenyl 2,4-di-O-acetyl-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