p-[2-(benzyloxycarbonyl)ethyl]phenyl β-D-galactopyranoside | 359686-45-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-[2-(benzyloxycarbonyl)ethyl]phenyl β-D-galactopyranoside
• 英文别名: benzyl 3-[4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]propanoate
• CAS: 359686-45-6
• 化学式: C₂₂H₂₆O₈
• 分子量: 418.444
• InChiKey: YWCYBWRYXUEZNS-WHCFWRGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-[2-(benzyloxycarbonyl)ethyl]phenyl β-D-galactopyranoside 在 palladium dihydroxide 、 palladium on activated charcoal 吡啶 、 18-冠醚-6 、 氢气 、 叠氮化四丁基铵 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三丁基氧化锡 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 85.5h， 生成 p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 2-acetamido-2-deoxy-4-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
• 作为产物：
  描述：

  p-[2-(benzyloxycarbonyl)ethyl]phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 苯甲醇钠 作用下， 以 苯甲醇 为溶剂， 反应 1.0h， 以74%的产率得到p-[2-(benzyloxycarbonyl)ethyl]phenyl 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

文献信息

• SYNTHESIS OF NEW GLYCOPOLYMERS CONTAINING β-<scp>D</scp>-MANNOPYRANOSE, AND<i>C</i>-2-SUBSTITUTED β-<scp>D</scp>-MANNOPYRANOSE RESIDUES AS A NEW CLASS OF INHIBITOR
  作者：Shoji Akai、Yasuhiro Kajihara、Yasuhiko Nagashima、Masugu Kamei、Junko Arai、Masami Bito、Ken-ichi Sato

  DOI：10.1081/car-100103953

  日期：2001.3.31

  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.