(4aR,6R,7R,8S,8aR)-2-Phenyl-6-(2-propyl-pentyloxy)-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol | 190442-98-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,6R,7R,8S,8aR)-2-Phenyl-6-(2-propyl-pentyloxy)-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 190442-98-9
• 化学式: C₄₈H₆₀O₁₀
• 分子量: 796.998
• InChiKey: KCUAXRXCZUQMNH-NBZNSZCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.31
• 重原子数：
  58.0
• 可旋转键数：
  19.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  103.3
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (4aR,6R,7R,8S,8aR)-2-Phenyl-6-(2-propyl-pentyloxy)-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 在 palladium on activated charcoal 氢气 、 sodium methylate 、 三氧化硫吡啶 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 29.0h， 生成 2-(propyl)pentyl O-(α-L-fucopyranosyl)-(1->2)-3-O-sulfo-β-D-galactopyranoside sodium 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：

  (4aR,6R,7R,8S,8aS)-8-(4-Methoxy-benzyloxy)-2-phenyl-6-(2-propyl-pentyloxy)-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine 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 2.0h， 以40%的产率得到(4aR,6R,7R,8S,8aR)-2-Phenyl-6-(2-propyl-pentyloxy)-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol
  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