phenyl 3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside | 208661-98-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside
• CAS: 208661-98-7
• 化学式: C₂₀H₂₄O₅S
• 分子量: 376.474
• InChiKey: RPXHNXQOFNWSKW-MMCWTAFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 MS-4 Angstroem 、 sodium methylate 、 三氧化硫吡啶 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 10.5h， 生成 2-(tetradecyl)hexadecyl O-(2,4-di-O-benzyl-3-O-sulfo-α-L-fucopyranosyl)-(1->2)-4,6-O-benzylidene-3-O-sulfo-β-D-galactopyranoside disodium salt
  参考文献：
  名称：

  Synthetic Studies on Selectin Ligands/Inhibitors: Synthesis and Inhibitory Activity of 2-O-Fucosyl Sulfatides Containing 2-Branched Fatty Alkyl Residues in Place of Ceramide

  摘要：

  To investigate the biological selectin-ligand interactions, four sulfated 2-0-alpha-L-fucopyranosyl beta-D-galactopyranosides containing 2-branched fatty-alkyl residues in place of ceramide have been systematically synthesized. The target glycolipids were assayed for their ability to block the adhesion of HL-60 cells to immobilized P-, L-and E-selectin. Among them, 2-O-alpha-L-fucopyranosyl sulfatide, which is anchored with 2-(tetradecyl) hexadecyl residue showed significantly more potency of the blocking adhesion to P- and L-selectins.

  DOI：

  10.1080/07328309808002905
• 作为产物：
  描述：

  4-甲氧基氯苄 、 phenyl 6-deoxy-1-thio-β-L-galactopyranoside 在 四丁基碘化铵 、 二正丁基氧化锡 作用下， 生成 phenyl 3-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Synthetic Studies on Selectin Ligands/Inhibitors: Synthesis and Inhibitory Activity of 2-O-Fucosyl Sulfatides Containing 2-Branched Fatty Alkyl Residues in Place of Ceramide

  摘要：

  To investigate the biological selectin-ligand interactions, four sulfated 2-0-alpha-L-fucopyranosyl beta-D-galactopyranosides containing 2-branched fatty-alkyl residues in place of ceramide have been systematically synthesized. The target glycolipids were assayed for their ability to block the adhesion of HL-60 cells to immobilized P-, L-and E-selectin. Among them, 2-O-alpha-L-fucopyranosyl sulfatide, which is anchored with 2-(tetradecyl) hexadecyl residue showed significantly more potency of the blocking adhesion to P- and L-selectins.

  DOI：

  10.1080/07328309808002905