2-amino-2-deoxy-D-galactose hydrazone | 131158-04-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-2-deoxy-D-galactose hydrazone
• CAS: 131158-04-8
• 化学式: C₆H₁₅N₃O₄
• 分子量: 193.203
• InChiKey: SNUXGKIHLBLRSZ-KCDKBNATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.67
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  145.32
• 氢给体数：
  6.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-amino-2-deoxy-D-galactose hydrazone 、 乙酰丙酮 以 水 为溶剂， 反应 2.0h， 生成 (2R,3R,4R,5R,6R)-5-Amino-6-(3,5-dimethyl-pyrazol-1-yl)-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 、 (2R,3R,4R,5R,6S)-5-Amino-6-(3,5-dimethyl-pyrazol-1-yl)-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 、 (R)-1-[(2R,3R,4R,5R)-4-Amino-5-(3,5-dimethyl-pyrazol-1-yl)-3-hydroxy-tetrahydro-furan-2-yl]-ethane-1,2-diol 、 (R)-1-[(2R,3R,4R,5S)-4-Amino-5-(3,5-dimethyl-pyrazol-1-yl)-3-hydroxy-tetrahydro-furan-2-yl]-ethane-1,2-diol
  参考文献：
  名称：

  Heterocyclic derivatives of sugars: an NMR study of the formation of 1-glycosyl-3,5-dimethyl-1 H-pyrazoles from hydrazones

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(97)00007-4
• 作为产物：
  描述：

  Galactosamine 在 一水合肼 作用下， 以 水 为溶剂， 生成 2-amino-2-deoxy-D-galactose hydrazone
  参考文献：
  名称：

  Heterocyclic derivatives of sugars: an NMR study of the formation of 1-glycosyl-3,5-dimethyl-1 H-pyrazoles from hydrazones

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(97)00007-4

文献信息

• A comparison of the results of sequential hydrazinolysis-nitrosation and alkali-mediated cleavage-nitrosation of theO-linked oligosaccharides of gastric mucus glycoproteins
  作者：Steven R. Carter、J. Michael Williams、John R. Clamp

  DOI：10.1016/0008-6215(90)80138-s

  日期：1990.9

  Analysis of the oligosaccharides released from pig gastric mucus glycopolypeptides by hydrazinolysis showed that degradation had occurred. Nitrosation of the products followed by reduction gave a mixture that had a low content of 2,5-anhydro-D-talitol, which implied destruction of much of the terminal reducing 2-amino-2-deoxy-D-galactose. Under the conditions of hydrazinolysis, cellobiose was largely unchanged but laminaribiose gave a complex mixture that probably contained glucose hydrazone (13C-n.m.r. data). In order to avoid degradation, the hydrazinolysis-nitrosation sequence should be applied to the reduced oligosaccharides released on cleavage with alkali.