2-hydroxyethyl 2,3,4-tri-O-acetyl-β-D-6-deoxyglucopyranose | 1574641-28-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxyethyl 2,3,4-tri-O-acetyl-β-D-6-deoxyglucopyranose
• CAS: 1574641-28-3
• 化学式: C₁₄H₂₂O₉
• 分子量: 334.323
• InChiKey: MHUAWFHGBXQHMI-FXXKZNHDSA-N

物化性质

• 沸点：
  414.9±45.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  2-hydroxyethyl 2,3,4-tri-O-acetyl-β-D-6-deoxyglucopyranose 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到2-(2,3,4-tri-O-acetyl-6-deoxy-β-D-glucopyranosyloxy)ethyl(2-cyanoethyl)(N,N-diisopropyl)phosphoramidite
  参考文献：
  名称：

  Effects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate–DNA Stacking Interactions in Water

  摘要：

  Carbohydrate-aromatic interactions are highly relevant for many biological processes. Nevertheless, experimental data in aqueous solution relating structure and energetics for sugar-arene stacking interactions are very scarce. Here, we evaluate how structural variations in a monosaccharide including carboxyl, N-acetyl, fluorine, and methyl groups affect stacking interactions with aromatic DNA bases. We find small differences on stacking interaction among the natural carbohydrates examined. The presence of fluorine atoms within the pyranose ring slightly increases the interaction with the C-G DNA base pair. Carbohydrate hydrophobicity is the most determinant factor. However, gradual increase in hydrophobicity of the carbohydrate does not translate directly into a steady growth in stacking interaction. The energetics correlates better with the amount of apolar surface buried upon sugar stacking on top of the aromatic DNA base pair.

  DOI：

  10.1021/jo402700y
• 作为产物：
  描述：

  乙二醇 、 2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranosyl bromide 在 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以44%的产率得到2-hydroxyethyl 2,3,4-tri-O-acetyl-β-D-6-deoxyglucopyranose
  参考文献：
  名称：

  Effects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate–DNA Stacking Interactions in Water

  摘要：

  Carbohydrate-aromatic interactions are highly relevant for many biological processes. Nevertheless, experimental data in aqueous solution relating structure and energetics for sugar-arene stacking interactions are very scarce. Here, we evaluate how structural variations in a monosaccharide including carboxyl, N-acetyl, fluorine, and methyl groups affect stacking interactions with aromatic DNA bases. We find small differences on stacking interaction among the natural carbohydrates examined. The presence of fluorine atoms within the pyranose ring slightly increases the interaction with the C-G DNA base pair. Carbohydrate hydrophobicity is the most determinant factor. However, gradual increase in hydrophobicity of the carbohydrate does not translate directly into a steady growth in stacking interaction. The energetics correlates better with the amount of apolar surface buried upon sugar stacking on top of the aromatic DNA base pair.

  DOI：

  10.1021/jo402700y