2-deoxy-2-(2-methyl-4-nitroimidazol-1-yl)-D-galactitol | 855160-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-deoxy-2-(2-methyl-4-nitroimidazol-1-yl)-D-galactitol
• 英文别名: (2R,3R,4R,5S)-5-(2-methyl-4-nitroimidazol-1-yl)hexane-1,2,3,4,6-pentol
• CAS: 855160-12-2
• 化学式: C₁₀H₁₇N₃O₇
• 分子量: 291.261
• InChiKey: DSRZCIJRVMDYDF-WDQPUEAGSA-N

物化性质

• 熔点：
  120-123 °C
• 沸点：
  706.7±60.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  165
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-deoxy-2-(2-methyl-4-nitroimidazol-1-yl)-D-galactitol 、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 以29%的产率得到1,3,4,5,6-penta-O-acetyl-2-deoxy-2-(2-methyl-4-nitroimidazol-1-yl)-D-galactitol
  参考文献：
  名称：

  Synthesis of 2-deoxy-2-(4-nitroimidazol-1-yl)-d-alditols

  摘要：

  Small molecules possessing defined configuration at centres of chirality provide a valuable chiral pool. Among different strategies applied for modification of chiral compounds, the most common is to begin with a single stereoisomer and use a synthesis that does not affect the chiral centres. The ANRORC type reaction has been applied for conversion of unprotected 2-amino-2-deoxy-D-hexopyranoses into 2-deoxy-2-(4-nitroimidazol-1-yl)-D-hexopyranoses in a reaction of some 2-aminosugars with 1,4-dinitroimidazoles. The reaction occurs with retention of configuration at C-2 of sugar ring. The products of the reaction were obtained as anomeric mixtures and separated into anomers after acetylation followed by column chromatography. 2-Deoxy-2-(4-nitroimidazol-1-yl)-D-hexopyranoses treated with sodium borohydride in methanolic solution gave the corresponding 2-deoxy-2-(4-nitroimidazol-l-yl)-D-hexitols, characterised as per-O-acetylated derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.03.005
• 作为产物：
  描述：

  D-(+)-galactosamine hydrochloride 在 sodium tetrahydroborate 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 2-deoxy-2-(2-methyl-4-nitroimidazol-1-yl)-D-galactitol
  参考文献：
  名称：

  Synthesis of 2-deoxy-2-(4-nitroimidazol-1-yl)-d-alditols

  摘要：

  Small molecules possessing defined configuration at centres of chirality provide a valuable chiral pool. Among different strategies applied for modification of chiral compounds, the most common is to begin with a single stereoisomer and use a synthesis that does not affect the chiral centres. The ANRORC type reaction has been applied for conversion of unprotected 2-amino-2-deoxy-D-hexopyranoses into 2-deoxy-2-(4-nitroimidazol-1-yl)-D-hexopyranoses in a reaction of some 2-aminosugars with 1,4-dinitroimidazoles. The reaction occurs with retention of configuration at C-2 of sugar ring. The products of the reaction were obtained as anomeric mixtures and separated into anomers after acetylation followed by column chromatography. 2-Deoxy-2-(4-nitroimidazol-1-yl)-D-hexopyranoses treated with sodium borohydride in methanolic solution gave the corresponding 2-deoxy-2-(4-nitroimidazol-l-yl)-D-hexitols, characterised as per-O-acetylated derivatives. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.03.005