methyl 4-O-methyl-β-D-galactopyranoside | 25029-36-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-methyl-β-D-galactopyranoside
• 英文别名: Methyl 4-O-methyl-β-D-galactopyranosid；(2R,3R,4R,5R,6R)-6-(hydroxymethyl)-2,5-dimethoxyoxane-3,4-diol
• CAS: 25029-36-1
• 化学式: C₈H₁₆O₆
• 分子量: 208.211
• InChiKey: YEEFEWNECFNTEE-UIAUGNHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 methyl 4-O-methyl-β-D-galactopyranoside 在 三氯化锑 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 2.0h， 以71.8%的产率得到methyl-(O²,O⁴-dimethyl-β-D-galactopyranoside)
  参考文献：
  名称：

  在过渡金属氯化物和硼酸存在下用重氮甲烷对甲基吡喃葡萄糖苷进行区域选择性甲基化

  摘要：

  摘要研究了在过渡金属氯化物和硼酸存在下，许多戊糖，己糖，6-脱氧己糖，尿酸甲酯及其甲基醚的甲基吡喃糖苷与重氮甲烷的部分甲基化。发现戊糖和6-脱氧己糖的甲基糖苷中锡（II），锑（III）和钛（IV）氯化物以及硼酸主要促进OH-3的取代，但被铈（III）和锌的取代（II）观察到盐主要取代了OH-2。在所有情况下，甲基β-1-鼠李糖吡喃糖苷的甲基化表现出较高的OH-2反应性。在氯化锡（II），锑（III）和铈（III）的存在下，己糖甲基糖苷的甲基化反应主要产生了3-甲基醚。不参与进一步络合的3-甲基醚 积聚高达50-80％的反应混合物（95％至100％的单甲醚馏分）。建议用于许多糖的方便的甲基醚的合成。

  DOI：

  10.1016/s0008-6215(99)00044-0
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 、 碘甲烷 在 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 4-O-methyl-β-D-galactopyranoside 、 methyl 6-O-methyl-β-D-galactopyranoside 、 methyl 3-O-methyl-β-D-galactopyranoside 、 methyl 2-O-methyl-β-D-galactopyranoside
  参考文献：
  名称：

  Application of NMR Based Binding Assays to Identify Key Hydroxy Groups for Intermolecular Recognition

  摘要：

  In general, few functional groups are sufficient for the binding of ligands to receptor proteins. For carbohydrates, characteristically spaced hydroxy groups often determine the binding affinity. Key functional groups may be identified by testing derivatives that have the potential sites blocked, which is most effectively achieved by simultaneous testing of all these derivatives. We employed such a parallel approach to identify the binding specificity of Sambucus nigra agglutinin (SNA), a lectin from elderberry. Compound libraries of randomly methylated O-methyl glycopyranosides were screened for binding activity toward SNA using trNOESY experiments, as well as 1D- and 2D-STD NMR experiments. The individual compounds have identical molecular weights and display rather similar physicochemical properties. Nevertheless, fast and reliable identification of the active compounds directly from the mixture was possible. The results are consistent with earlier biochemical work, showing that SNA has a binding specificity for D-galactose with the hydroxy functions at carbon atoms C3 and C4 of methyl beta-D-galactopyranoside being critically important for binding. Finally, we show that the screening protocol can be extended to heteronuclear STD pulse sequences if C-13-labeled derivatives are present in the library.

  DOI：

  10.1021/ja0001916