methyl 6-deoxy-6-[N'-(6-amino-6-deoxy-β-D-glucopyranosyl)thioureido]-α-D-glucopyranoside | 675616-86-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-deoxy-6-[N'-(6-amino-6-deoxy-β-D-glucopyranosyl)thioureido]-α-D-glucopyranoside
• CAS: 675616-86-1
• 化学式: C₁₄H₂₇N₃O₉S
• 分子量: 413.449
• InChiKey: LPFSWEWBALLBSC-VHGSIDFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.33
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  199.15
• 氢给体数：
  9.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 6-deoxy-6-[N'-(6-amino-6-deoxy-β-D-glucopyranosyl)thioureido]-α-D-glucopyranoside 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 methyl 6-deoxy-6-[N'-[6-deoxy-6-(N'-β-D-glucopyranosylthioureido)-β-D-glucopyranosyl]thioureido]-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：

  2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-D-glucopyranosyl isothiocyanate 在 1,3-丙二硫醇 、 sodium methylate 、 三乙胺 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 23.0h， 生成 methyl 6-deoxy-6-[N'-(6-amino-6-deoxy-β-D-glucopyranosyl)thioureido]-α-D-glucopyranoside
  参考文献：
  名称：

  线性和树枝状硫脲连接的糖基低聚物的合成和结构

  摘要：

  已经开发出一种生产含有硫脲糖间桥的非天然糖基低聚物的有效策略。由于硫脲的氢键能力，这些低聚物中硫脲基团的存在应促进与多磷酸盐（包括核酸）的结合。此外，由于与硫羰基相邻的键上的氢键和旋转限制的相互作用，由硫脲基团构建的糖基低聚物应形成复杂的二级和三级结构。在此，描述了线性和树枝状结构的制备和构象特性。这种合成方法依赖于全乙酰化叠氮基异硫氰酸酯和完全未保护的胺官能化生长低聚物的偶联。半乙酰化硫脲加合物的脱乙酰化和叠氮基的还原允许进入新的偶联循环。该程序非常通用，应该很容易扩展到面向分子多样性的固相方法，并将允许研究分子间相互作用。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200500472

文献信息

• Blanco, Jose L. Jimenez; Bootello, Purificacion; Mellet, Carmen Ortiz, Chemical Communications, 2004, # 1, p. 92 - 93
  作者：Blanco, Jose L. Jimenez、Bootello, Purificacion、Mellet, Carmen Ortiz、Gallego, Ricardo Gutierrez、Fernandez, Jose M. Garcia

  DOI：——

  日期：——