4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside | 903881-61-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• CAS: 903881-61-8
• 化学式: C₂₆H₃₅BO₁₂
• 分子量: 550.368
• InChiKey: YLXKXHWNSZVVHW-OYTPZHDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 四(三苯基膦)钯 sodium methylate 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 21.5h， 生成 4-β-D-galactopyranosyl-3'-β-D-glucopyranosyl-biphenyl
  参考文献：
  名称：

  Antagonists of the myelin-associated glycoprotein: A new class of tetrasaccharide mimics

  摘要：

  The tetrasaccharide substructure 1 of the ganglioside GQ1b alpha shows a remarkable affinity for the myelin-associated glycoprotein (MAG). In the search for structurally simplified and pharmacokinetically improved mimics of 1, biphenyl was identified as a feasible replacement for the core disaccharide Ga1 beta(1-3)Ga1NAc according to saturation transfer difference (STD) NMR and molecular modeling investigations. Using Suzuki coupling, a convergent synthesis of the mimics was achieved. To optimize the yields of the coupling reactions, the catalytic effects of microwave irradiation and conventional heating were compared. The biological evaluation of mimics 3 and 4 was performed in a competitive target-based assay. It was found that the relative inhibitory potency (rIP) of antagonist 3 was clearly enhanced in comparison to the reference trisaccharide 2, despite the former having a much simpler structure. In addition to the improved synthetic feasibility, an increase of the partition coefficient between octanol and water (log P), and therefore a beneficial change in the pharmacokinetic properties of 3 and 4 was achieved. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.007
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 1,1'-双(二苯基膦)二茂铁 、 sodium hydroxide 、 potassium acetate 、 苄基三乙基溴化铵 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Antagonists of the myelin-associated glycoprotein: A new class of tetrasaccharide mimics

  摘要：

  The tetrasaccharide substructure 1 of the ganglioside GQ1b alpha shows a remarkable affinity for the myelin-associated glycoprotein (MAG). In the search for structurally simplified and pharmacokinetically improved mimics of 1, biphenyl was identified as a feasible replacement for the core disaccharide Ga1 beta(1-3)Ga1NAc according to saturation transfer difference (STD) NMR and molecular modeling investigations. Using Suzuki coupling, a convergent synthesis of the mimics was achieved. To optimize the yields of the coupling reactions, the catalytic effects of microwave irradiation and conventional heating were compared. The biological evaluation of mimics 3 and 4 was performed in a competitive target-based assay. It was found that the relative inhibitory potency (rIP) of antagonist 3 was clearly enhanced in comparison to the reference trisaccharide 2, despite the former having a much simpler structure. In addition to the improved synthetic feasibility, an increase of the partition coefficient between octanol and water (log P), and therefore a beneficial change in the pharmacokinetic properties of 3 and 4 was achieved. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.007