2-<(4-Methoxybenzyl)oxy>ethyl 2,6-di-O-benzyl-β-D-galactopyranoside | 163400-61-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<(4-Methoxybenzyl)oxy>ethyl 2,6-di-O-benzyl-β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-6-[2-[(4-methoxyphenyl)methoxy]ethoxy]-5-phenylmethoxy-2-(phenylmethoxymethyl)oxane-3,4-diol
• CAS: 163400-61-1
• 化学式: C₃₀H₃₆O₈
• 分子量: 524.611
• InChiKey: DXGYTYPFGMHYRA-HBMYTODVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  95.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  溴乙酸乙酯 、 2-<(4-Methoxybenzyl)oxy>ethyl 2,6-di-O-benzyl-β-D-galactopyranoside 在 四丁基碘化铵 、 二正丁基氧化锡 作用下， 生成 (4aS,5R,7R,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-[2-(4-methoxy-benzyloxy)-ethoxy]-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one
  参考文献：
  名称：

  Synthesis of Biologically Active Sialyl Lewis X Mimetics

  摘要：

  The design and synthesis of two sialyl Lewis X (SLe(x)) mimetics are described. In the design of mimetic 1, an ethylene glycol linkage is used to bridge the fucose and galactose moiety, and a carboxymethyl group is placed in the 3-OH position of the galactose residue to provide the negative charge which is believed to be essential for binding to (E)-selectin. In the design of mimetic 2, a D-tartaric acid derivative is used to provide the trans-dihydroxyl groups originally from the glucosamine moiety for the linkage of the fucose and the carboxypentyl groups. At a concentration of 1.5 mM, 1 inhibits 50% of the binding of SLe(x) glycoconjugate to immobilized recombinant (E)-selectin, while 2 has an IC50 of 10 mM. Mimetic 1 is also found to be stable toward alpha-L-fucosidase. Results from the ROESY and COSY experiments indicate that compound 1 is conformationally flexible, which may explain its relatively weak activity compared to SLe(x) (IC50 = 0.8 mM).

  DOI：

  10.1021/jo00115a027
• 作为产物：
  描述：

  (3aS,4R,6R,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-[2-(4-methoxy-benzyloxy)-ethoxy]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 在 溶剂黄146 作用下， 反应 1.0h， 生成 2-<(4-Methoxybenzyl)oxy>ethyl 2,6-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Biologically Active Sialyl Lewis X Mimetics

  摘要：

  The design and synthesis of two sialyl Lewis X (SLe(x)) mimetics are described. In the design of mimetic 1, an ethylene glycol linkage is used to bridge the fucose and galactose moiety, and a carboxymethyl group is placed in the 3-OH position of the galactose residue to provide the negative charge which is believed to be essential for binding to (E)-selectin. In the design of mimetic 2, a D-tartaric acid derivative is used to provide the trans-dihydroxyl groups originally from the glucosamine moiety for the linkage of the fucose and the carboxypentyl groups. At a concentration of 1.5 mM, 1 inhibits 50% of the binding of SLe(x) glycoconjugate to immobilized recombinant (E)-selectin, while 2 has an IC50 of 10 mM. Mimetic 1 is also found to be stable toward alpha-L-fucosidase. Results from the ROESY and COSY experiments indicate that compound 1 is conformationally flexible, which may explain its relatively weak activity compared to SLe(x) (IC50 = 0.8 mM).

  DOI：

  10.1021/jo00115a027

文献信息

• Synthesis of Biologically Active Sialyl Lewis X Mimetics
  作者：Hongmei Huang、Chi-Huey Wong

  DOI：10.1021/jo00115a027

  日期：1995.5

  The design and synthesis of two sialyl Lewis X (SLe(x)) mimetics are described. In the design of mimetic 1, an ethylene glycol linkage is used to bridge the fucose and galactose moiety, and a carboxymethyl group is placed in the 3-OH position of the galactose residue to provide the negative charge which is believed to be essential for binding to (E)-selectin. In the design of mimetic 2, a D-tartaric acid derivative is used to provide the trans-dihydroxyl groups originally from the glucosamine moiety for the linkage of the fucose and the carboxypentyl groups. At a concentration of 1.5 mM, 1 inhibits 50% of the binding of SLe(x) glycoconjugate to immobilized recombinant (E)-selectin, while 2 has an IC50 of 10 mM. Mimetic 1 is also found to be stable toward alpha-L-fucosidase. Results from the ROESY and COSY experiments indicate that compound 1 is conformationally flexible, which may explain its relatively weak activity compared to SLe(x) (IC50 = 0.8 mM).