(S)-2-{(2S,4aR,6R,7R,8R,8aS)-7-Hydroxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-3-phenyl-propionic acid benzyl ester | 187402-09-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-{(2S,4aR,6R,7R,8R,8aS)-7-Hydroxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-3-phenyl-propionic acid benzyl ester
• CAS: 187402-09-1
• 化学式: C₆₂H₆₈O₁₃
• 分子量: 1021.21
• InChiKey: IXCZLFDXPVUZBR-GUIRNXHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.77
• 重原子数：
  75.0
• 可旋转键数：
  21.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  138.83
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (S)-2-{(2S,4aR,6R,7R,8R,8aS)-7-Hydroxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-3-phenyl-propionic acid benzyl ester 在 palladium dihydroxide 氢气 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以78%的产率得到sodium (2S) 2-O-{1-O-[(1R,2R) 2-O-(α-L-fucopyranosyl)cyclohexyl]-β-D-galactopyranos-3-yl}-3-phenylpropanoate
  参考文献：
  名称：

  Development of Tools for the Design of Selectin Antagonists

  摘要：

  AbstractA molecular modeling tool for the rational design of E‐selectin antagonists based on the lead structure sialyl Lewisx has been developed. The binding affinity to the receptor is considerably influenced by the entropy and consequently by the antagonist's ability to place its pharmacophores in an optimal spatial arrangement, i.e., by its preorganization for binding. The computational model assesses the preorganization of a potential selectin antagonist with the aid of Monte Carlo (jumping between wells)/stochastic dynamics [MC(JBW)/SD] simulations. The model has been validated by correlating preorganization and bioactivity of several selectin antagonists. The results suggest that only preorganized compounds are likely to bind to E‐selectin.

  DOI：

  10.1002/chem.19970031006
• 作为产物：
  描述：

  (2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol 在 camphor-10-sulfonic acid 、 二正丁基氧化锡 、 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 4.75h， 生成 (S)-2-{(2S,4aR,6R,7R,8R,8aS)-7-Hydroxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-3-phenyl-propionic acid benzyl ester
  参考文献：
  名称：

  Development of Tools for the Design of Selectin Antagonists

  摘要：

  AbstractA molecular modeling tool for the rational design of E‐selectin antagonists based on the lead structure sialyl Lewisx has been developed. The binding affinity to the receptor is considerably influenced by the entropy and consequently by the antagonist's ability to place its pharmacophores in an optimal spatial arrangement, i.e., by its preorganization for binding. The computational model assesses the preorganization of a potential selectin antagonist with the aid of Monte Carlo (jumping between wells)/stochastic dynamics [MC(JBW)/SD] simulations. The model has been validated by correlating preorganization and bioactivity of several selectin antagonists. The results suggest that only preorganized compounds are likely to bind to E‐selectin.

  DOI：

  10.1002/chem.19970031006