(4aR,6R,7R,8R,8aS)-8-(4-Methoxy-benzyloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol | 190443-01-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4aR,6R,7R,8R,8aS)-8-(4-Methoxy-benzyloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
• 英文别名: (4aR,6R,7R,8R,8aS)-8-[(4-methoxyphenyl)methoxy]-2-phenyl-6-(2-propylpentoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 190443-01-7
• 化学式: C₂₉H₄₀O₇
• 分子量: 500.632
• InChiKey: CHFSMMCVTSEWHK-SDDOYEAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4aR,6R,7R,8R,8aS)-8-(4-Methoxy-benzyloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 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 、 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 8.0h， 生成
  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：

  (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(2-propylpentoxy)oxane-3,4,5-triol 在 硫酸 、 四丁基碘化铵 、 二正丁基氧化锡 作用下， 以 四氢呋喃 为溶剂， 反应 68.0h， 生成 (4aR,6R,7R,8R,8aS)-8-(4-Methoxy-benzyloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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

文献信息

• US5869460A
  申请人：——

  公开号：US5869460A

  公开（公告）日：1999-02-09
• Synthetic Studies on Selectin Ligands/Inhibitors: Synthesis and Inhibitory Activity of 2-<i>O</i>-Fucosyl Sulfatides Containing 2-Branched Fatty Alkyl Residues in Place of Ceramide
  作者：Takao Ikami、Takuji Kakigami、Kunihisa Baba、Hitoshi Hamajima、Takahito Jomori、Toshinao Usui、Yasuo Suzuki、Harunari Tanaka、Hideharu Ishida、Akira Hasegawa、Makoto Kiso

  DOI：10.1080/07328309808002905

  日期：1998.4

  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.