β-D-glucopyranosyl hydrazine | 190259-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-glucopyranosyl hydrazine
• 英文别名: 1-Deoxy-1-hydrazinyl-I(2)-D-glucopyranose；(2R,3R,4S,5S,6R)-2-hydrazinyl-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 190259-04-2
• 化学式: C₆H₁₄N₂O₅
• 分子量: 194.188
• InChiKey: QDCGKSGKHZOMKB-VFUOTHLCSA-N

物化性质

• 沸点：
  496.9±45.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  128
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  D-glucose hydrazon 在 一水合肼 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 β-D-glucopyranosyl hydrazine
  参考文献：
  名称：

  NMR Studies of Saccharide Hydrazones, Thiosemicarbazones and Azines: Model Compounds for Immobilisation Studies

  摘要：

  To evaluate possible chemical strategies for the solid-phase immobilization of sugars, studies on the formation and stability of hydrazones, thiosemicarbazones and azines of D-glucose and 2-acetamido-2-deoxy-D-glucose, and the subsequent release of sugars, were carried out. Hydrazone formation was observed to occur under milder conditions than previously reported, thereby minimising the accompanying N-deacetylation which occurs with N-acetamido sugars. The cyclic beta-pyranosyl structures of the saccharide hydrazones, thiosemicarbazones and azines were the preferred isomers in aqueous solution.

  DOI：

  10.1080/07328309808005766

文献信息

• Auge, Jacques; Lubin-Germain, Nadege, Journal of Carbohydrate Chemistry, 2000, vol. 19, # 3, p. 378 - 392
  作者：Auge, Jacques、Lubin-Germain, Nadege

  DOI：——

  日期：——
• Heterocyclic derivatives of sugars: an NMR study of the formation of 1-glycosyl-3,5-dimethyl-1 H-pyrazoles from hydrazones
  作者：Warren C Kett、Michael Batley、John W Redmond

  DOI：10.1016/s0008-6215(97)00007-4

  日期：1997.4

  Hydrazones were prepared by treatment of monosaccharides and disaccharides with hydrazine hydrate and converted in high yield to mixtures of 1-glycosyl-3,5-dimethyl-1 H-pyrazoles by reaction with pentan-2,4-dione (acetylacetone). The isomeric products were separated by HPLC and characterized by NMR spectroscopy. This represents a new approach to the introduction of a heteroaromatic label into sugars under nonacidic and nonreducing conditions, and it is a process likely to be especially useful for glycan hydrazones obtained from glycoproteins by hydrazinolysis or beta elimination in the presence of hydrazine. (C) 1997 Elsevier Science Ltd.
• Preparation, conformation, and mild hydrolysis of 1-glycosyl-2-acetylhydrazines of the hexoses, pentoses, 2-acetamido-2-deoxyhexoses, and fucose
  作者：Brad Bendiak

  DOI：10.1016/s0008-6215(97)00213-9

  日期：1997.10

  The title compounds were prepared and their conformations studied by H-1-NMR. Their acid hydrolysis under mild conditions was monitored by H-1-NMR. (C) 1997 Published by Elsevier Science Ltd.
• NMR Studies of Saccharide Hydrazones, Thiosemicarbazones and Azines: Model Compounds for Immobilisation Studies
  作者：Helen J. Tweeddale、John W. Redmond

  DOI：10.1080/07328309808005766

  日期：1998.1

  To evaluate possible chemical strategies for the solid-phase immobilization of sugars, studies on the formation and stability of hydrazones, thiosemicarbazones and azines of D-glucose and 2-acetamido-2-deoxy-D-glucose, and the subsequent release of sugars, were carried out. Hydrazone formation was observed to occur under milder conditions than previously reported, thereby minimising the accompanying N-deacetylation which occurs with N-acetamido sugars. The cyclic beta-pyranosyl structures of the saccharide hydrazones, thiosemicarbazones and azines were the preferred isomers in aqueous solution.