methyl 2-O-acetyl-3-deoxy-β-D-galactopyranoside | 1039443-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-acetyl-3-deoxy-β-D-galactopyranoside
• CAS: 1039443-03-2
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: BJRZSPDTRQOETG-FNCVBFRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.97
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2-O-acetyl-3-deoxy-β-D-galactopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 16.0h， 以98%的产率得到methyl 3-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Benzoboroxoles as Efficient Glycopyranoside-Binding Agents in Physiological Conditions: Structure and Selectivity of Complex Formation

  摘要：

  In contrast to normal boronic acids, o-hydroxymethyl phenylboronic acid (benzoboroxole) has the capability of complexing glycopyranosides efficiently in neutral water. The measurement of association constants with a panel of model hexopyranosides indicates that the preferred mode of binding is through a cis-3,4-diol, such as that found in galactopyranosides, and mass spectrometric studies support a 1: 1 binding stoichiometry. The complexation of glucopyranosides is weaker, and they are bound through their 4,6-diol unit. Although several factors may explain the exceptional carbohydrate-binding behavior of this class of hemiboronic acids, the relatively high Lewis acidity of benzoboroxoles is a likely contributing factor along with subtle factors such as intramolecular hydrogen bonds with other hydroxyl groups in the resulting anionic complex. These results with hexopyranosides suggest that biologically relevant cell-surface oligosaccharides could be targeted in water using oligomeric benzoboroxole receptors.

  DOI：

  10.1021/jo800788s
• 作为产物：
  描述：

  methyl 2-O-acetyl-4,6-O-benzylidene-3-deoxy-β-D-xylo-hexopyranoside 在 水 、 溶剂黄146 作用下， 反应 3.0h， 以83%的产率得到methyl 2-O-acetyl-3-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Benzoboroxoles as Efficient Glycopyranoside-Binding Agents in Physiological Conditions: Structure and Selectivity of Complex Formation

  摘要：

  In contrast to normal boronic acids, o-hydroxymethyl phenylboronic acid (benzoboroxole) has the capability of complexing glycopyranosides efficiently in neutral water. The measurement of association constants with a panel of model hexopyranosides indicates that the preferred mode of binding is through a cis-3,4-diol, such as that found in galactopyranosides, and mass spectrometric studies support a 1: 1 binding stoichiometry. The complexation of glucopyranosides is weaker, and they are bound through their 4,6-diol unit. Although several factors may explain the exceptional carbohydrate-binding behavior of this class of hemiboronic acids, the relatively high Lewis acidity of benzoboroxoles is a likely contributing factor along with subtle factors such as intramolecular hydrogen bonds with other hydroxyl groups in the resulting anionic complex. These results with hexopyranosides suggest that biologically relevant cell-surface oligosaccharides could be targeted in water using oligomeric benzoboroxole receptors.

  DOI：

  10.1021/jo800788s