benzyl 2,3,6-tri-O-benzyl-4-O-(1-imidazolyl thiocarbonyl)-D-glucopyranoside | 784179-21-1

• 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-4-O-(1-imidazolyl thiocarbonyl)-D-glucopyranoside
• CAS: 784179-21-1
• 化学式: C₃₈H₃₈N₂O₆S
• 分子量: 650.796
• InChiKey: UBTIPNCBPSKHBL-YGMGGQQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  73.2
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,6-tri-O-benzyl-4-O-(1-imidazolyl thiocarbonyl)-D-glucopyranoside 在 n-butyl tin hydride 、 偶氮二异丁腈 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以68%的产率得到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 、 甲苯 为溶剂， 反应 22.0h， 生成 benzyl 2,3,6-tri-O-benzyl-4-O-(1-imidazolyl thiocarbonyl)-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