(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 | 163400-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (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
• 英文别名: (4aS,5R,7R,8R,8aS)-7-[2-[(4-methoxyphenyl)methoxy]ethoxy]-8-phenylmethoxy-5-(phenylmethoxymethyl)-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-3-one
• CAS: 163400-62-2
• 化学式: C₃₂H₃₆O₉
• 分子量: 564.632
• InChiKey: IBADPNPRJMQZFO-YGMVDIOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (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 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 以88%的产率得到(4aS,5R,7R,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-(2-hydroxy-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：

  2-<(4-Methoxybenzyl)oxy>ethyl 2,6-di-O-benzyl-3-<(ethoxycarbonyl)methyl>-β-D-galactopyranoside 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以60%的产率得到(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