(2R,3S,4S,5R,6S)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-5(benzyloxycarbonyloxy)-2-(benzyloxymethyl)-6-(ethylthio)tetrahydro-2H-pyran-3-yl 1-naphtoate | 1403603-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,3S,4S,5R,6S)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-5(benzyloxycarbonyloxy)-2-(benzyloxymethyl)-6-(ethylthio)tetrahydro-2H-pyran-3-yl 1-naphtoate
• CAS: 1403603-72-4
• 化学式: C₅₀H₄₈O₁₀S
• 分子量: 840.991
• InChiKey: LUVVMUUMRKSNGL-TVMPMPFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.52
• 重原子数：
  61.0
• 可旋转键数：
  18.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  115.82
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6S)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-5(benzyloxycarbonyloxy)-2-(benzyloxymethyl)-6-(ethylthio)tetrahydro-2H-pyran-3-yl 1-naphtoate 、 (2R,3R)-dimethyl-2-(3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-(3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate 在 溴 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 以58%的产率得到(2R,3R)-dimethyl 2-((2S,3R,4S,5S,6R)-5-(1-naphthoyloxy)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-3-(benzyloxycarbonyloxy)-6-(benzyloxymethyl)tetrahydro-2Hpyran-2-yloxy)-3-((2S,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yloxy)succinate
  参考文献：
  名称：

  A New Approach to Explore the Binding Space of Polysaccharide-Based Ligands: Selectin Antagonists

  摘要：

  The discovery of molecules that interfere with the binding of a ligand to a receptor remains a topic of great interest in medicinal chemistry. Herein, we report that a monosaccharide unit of a polysaccharide ligand can be replaced advantageously by a conformationally locked acyclic molecular entity. A cyclic component of the selectin ligand Sialyl Lewis(x), GlcNAc, is replaced by an acyclic tether, tartaric esters, which link two saccharide units. The conformational bias of this acyclic tether originates from the minimization of intramolecular dipole-dipole interaction and the gauche effect. The evaluation of the binding of these derivatives to P-selectin was measured by surface plasmon resonance spectroscopy. The results obtained in our pilot study suggest that the discovery of tunable tethers could facilitate the exploration of the carbohydrate recognition domain of various receptors.

  DOI：

  10.1021/ml300263x
• 作为产物：
  描述：

  ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-thiogalactopyranoside 在 4-二甲氨基吡啶 、 sodium methylate 、 sodium hydride 、 二正丁基氧化锡 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.58h， 生成 (2R,3S,4S,5R,6S)-4-((R)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-yloxy)-5(benzyloxycarbonyloxy)-2-(benzyloxymethyl)-6-(ethylthio)tetrahydro-2H-pyran-3-yl 1-naphtoate
  参考文献：
  名称：

  A New Approach to Explore the Binding Space of Polysaccharide-Based Ligands: Selectin Antagonists

  摘要：

  The discovery of molecules that interfere with the binding of a ligand to a receptor remains a topic of great interest in medicinal chemistry. Herein, we report that a monosaccharide unit of a polysaccharide ligand can be replaced advantageously by a conformationally locked acyclic molecular entity. A cyclic component of the selectin ligand Sialyl Lewis(x), GlcNAc, is replaced by an acyclic tether, tartaric esters, which link two saccharide units. The conformational bias of this acyclic tether originates from the minimization of intramolecular dipole-dipole interaction and the gauche effect. The evaluation of the binding of these derivatives to P-selectin was measured by surface plasmon resonance spectroscopy. The results obtained in our pilot study suggest that the discovery of tunable tethers could facilitate the exploration of the carbohydrate recognition domain of various receptors.

  DOI：

  10.1021/ml300263x