methyl 6-deoxy-6-[N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thioureido]-α-D-glucopyranoside | 250329-49-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 6-deoxy-6-[N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thioureido]-α-D-glucopyranoside
• 英文别名: methyl 6-deoxy-6-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthioureido)-α-D-glucopyranoside
• CAS: 250329-49-8
• 化学式: C₂₂H₃₄N₂O₁₄S
• 分子量: 582.583
• InChiKey: SEGMVPSFUUIGKJ-LPYSQXSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.01
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  217.64
• 氢给体数：
  5.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  methyl 6-deoxy-6-[N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thioureido]-α-D-glucopyranoside 在 吡啶 、 sodium methylate 、 三氟乙酸 、 mercury(II) oxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 2.75h， 生成 methyl 6-deoxy-6-[N"-(β-D-glucopyranosyl)ureido]-α-D-glucopyranoside
  参考文献：
  名称：

  Urea-, Thiourea-, and Guanidine-Linked Glycooligomers as Phosphate Binders in Water

  摘要：

  [GRAPHICS]beta-(1 -> 6)-Linked pseudodi- and pseudotrisaccharides incorporating alternating pseudoamide-type (urea, thiourea, guanidine) intersaccharide bridges have been prepared and evaluated as phosphate binders in water. The monosaccharide subunits induce the Z, Z rotameric form at the pseudoamide segments, thus favoring their participation in bidentate hydrogen-bond interactions with oxoanions. Moreover, the conformational properties about the anomeric C-1-N bonds and the sugar C-5-C-6 bonds privilege orientations that facilitate both the desolvation of the incoming anionic guest and the stabilization of the complex by cooperative interactions. Measurable association constants (K-as) toward dimethyl and, especially, phenyl phosphate were obtained from NMR titration experiments for both series of glucooligomers, the binding affinity being strongly dependent on the nature of the pseudoamide functionality. Guanidinium derivatives, for which charge neutralization was expected to contribute to phosphate binding, were superior to the neutral thiourea and urea derivatives (K-as=48-60 M-1 for 1:1 complexes with phenyl phosphate dianion). Interestingly, the thiourea oligomers exhibited association constants of the same order of magnitude (K-as=25-40 M-1), much higher than those observed for the urea analogues (K-as=2-3 M-1), which is ascribed to a less efficient solvation of the thiocarbonyl derivatives.

  DOI：

  10.1021/jo060360q
• 作为产物：
  描述：

  甲基-6-氨基-6-脱氧-alpha-d-吡喃葡萄糖苷 、 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 以 吡啶 为溶剂， 反应 2.0h， 以90%的产率得到methyl 6-deoxy-6-[N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thioureido]-α-D-glucopyranoside
  参考文献：
  名称：

  （1→6）-硫脲连接的假寡糖的合成及端基稳定性

  摘要：

  摘要报道了通过单-和二糖-过-O-乙酰化的糖基异硫氰酸酯与甲基6-氨基-6-脱氧-α-d-吡喃葡萄糖苷的偶联合成掺入硫脲糖间桥联的寡糖模拟物的方法。然而，在Zemplen脱乙酰基作用下，对于α-和β-d-甘露吡喃糖基硫脲基衍生物，观察到了意外的异构化反应。动力学研究表明，该异构化过程是碱催化的，并且强烈依赖于反应温度和反应时间。通过在0°C下进行最后一步，可以在没有差向异构的情况下获得完全未保护的化合物。在所有情况下，最终的伪低聚糖在室温下在没有碱的情况下在水溶液中都是稳定的。

  DOI：

  10.1016/s0008-6215(99)00141-x