benzyl 2,3,6-tri-O-benzyl-D-glucopyranoside | 784179-20-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,6-tri-O-benzyl-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R)-4,5,6-tris(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 784179-20-0
• 化学式: C₃₄H₃₆O₆
• 分子量: 540.656
• InChiKey: HYZRJGYIUDQFSY-BKJHVTENSA-N

物化性质

• 沸点：
  676.1±55.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  40.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,6-tri-O-benzyl-D-glucopyranoside 在 n-butyl tin hydride 、 偶氮二异丁腈 作用下， 以 甲苯 为溶剂， 反应 19.5h， 生成 benzyl 2,3,6-tri-O-benzyl-4-deoxy-D-xylo-hexopyranoside
  参考文献：
  名称：

  Thermodynamics of Binding of d-Galactose and Deoxy Derivatives thereof to the l-Arabinose-binding Protein

  摘要：

  We report the thermodynamics of binding Of D-galactose and deoxy derivatives thereof to the arabinose binding protein (ABP). The "intrinsic" (solute-solute) free energy of binding DeltaG(int)(0) at 308 K for the 1-, 2-, 3-, and 6-hydroxyl groups of galactose is remarkably constant (similar to-30 kJ/mol), despite the fact that each hydroxyl group subtends different numbers of hydrogen bonds in the complex. The substantially unfavorable enthalpy of binding (similar to30 W/mol) of 1-deoxygalactose, 2-deoxygalactose, and 3-deoxygalactose in comparison with galactose, cannot be readily accounted for by differences in solvation, suggesting that solute-solute hydrogen bonds are enthalpically significantly more favorable than solute-solvent hydrogen bonds. In contrast, the substantially higher affinity for 2-deoxygalactose in comparison with either 1-deoxygalactose or 3-deoxygalactose derives from differences in the solvation free energies of the free ligands.

  DOI：

  10.1021/ja048054m
• 作为产物：
  描述：

  benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranoside 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以68%的产率得到benzyl 2,3,6-tri-O-benzyl-D-glucopyranoside
  参考文献：
  名称：

  Thermodynamics of Binding of d-Galactose and Deoxy Derivatives thereof to the l-Arabinose-binding Protein

  摘要：

  We report the thermodynamics of binding Of D-galactose and deoxy derivatives thereof to the arabinose binding protein (ABP). The "intrinsic" (solute-solute) free energy of binding DeltaG(int)(0) at 308 K for the 1-, 2-, 3-, and 6-hydroxyl groups of galactose is remarkably constant (similar to-30 kJ/mol), despite the fact that each hydroxyl group subtends different numbers of hydrogen bonds in the complex. The substantially unfavorable enthalpy of binding (similar to30 W/mol) of 1-deoxygalactose, 2-deoxygalactose, and 3-deoxygalactose in comparison with galactose, cannot be readily accounted for by differences in solvation, suggesting that solute-solute hydrogen bonds are enthalpically significantly more favorable than solute-solvent hydrogen bonds. In contrast, the substantially higher affinity for 2-deoxygalactose in comparison with either 1-deoxygalactose or 3-deoxygalactose derives from differences in the solvation free energies of the free ligands.

  DOI：

  10.1021/ja048054m

文献信息

• [EN] INHIBITORS OF MALARIAL AND PLASMODIUM FALCIPARUM HEXOSE TRANSPORTER AND USES THEREOF<br/>[FR] INHIBITEURS DU TRANSPORTEUR D'HEXOSE DE LA MALARIA ET DE PLASMODIUM FALCIPARUM ET LEURS UTILISATIONS
  申请人：UNIV TSINGHUA

  公开号：WO2021155748A1

  公开（公告）日：2021-08-12

  Provided are molecules capable of binding to binding pockets of Plasmodium falciparum hexose transporter (PfHT) or analogs thereof and complexes comprising the same. Also provided herein are inhibitors of PfHT, pharmaceutical compositions comprising the inhibitors, and methods of using the inhibitors or the pharmaceutical compositions in the treatment of diseases associated with Plasmodium or PfHT or the killing or inhibiting the growth of Plasmodium. Provided are a set of structure coordinates of such binding pockets and method of using the set of structure coordinates to screen for and design compounds that are capable of binding to PfHT or analogs thereof.

  提供了能够结合到疟原虫己糖转运蛋白（PfHT）或其类似物的结合口袋的分子，以及包含这些分子的复合物。此外，还提供了PfHT的抑制剂，包含这些抑制剂的药物组合物，以及在治疗与疟原虫或PfHT相关的疾病或杀死或抑制疟原虫生长中使用这些抑制剂或药物组合物的方法。提供了这些结合口袋的结构坐标集合，并提供了使用这些结构坐标集合来筛选和设计能够结合到PfHT或其类似物的化合物的方法。