1-(α-D-arabinofuranosyl)-2-acetamidoimidazole | 250693-35-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: 1-(α-D-arabinofuranosyl)-2-acetamidoimidazole
• 英文别名: N-[1-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazol-2-yl]acetamide
• CAS: 250693-35-7
• 化学式: C₁₀H₁₅N₃O₅
• 分子量: 257.246
• InChiKey: SVEVDLBYYDLCCS-HXFLIBJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(α-D-arabinofuranosyl)-2-acetamidoimidazole 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以65%的产率得到1-(alpha-D-阿拉伯呋喃糖基)-1H-咪唑-2-胺
  参考文献：
  名称：

  Synthesis of Iodoaminoimidazole Arabinoside (IAIA): A Potential Reductive Metabolite of the Spect Imaging Agent, Iodoazomycin Arabinoside (IAZA)

  摘要：

  The stereospecific synthesis of 1-(5-deoxy-5-iodo-alpha-D-arabinofuranosyl)-2-aminoimidazole (iodoaminoimidazole arabinoside: IAIA, 2) is described. The reaction of the protected sugar bromide (8) and trifluoroacetamidoimidazole (10B) gave the coupled product (11B), which gave the free nucleoside (4) on deblocking. It was identical with AIA obtained by reduction of AZA (azomycin arabinoside), whose anomeric configuration was found to be a by the X-ray crystallography.

  DOI：

  10.1080/07328319908044860
• 作为产物：
  描述：

  1-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2-acetamidoimidazole 在 氨 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以73%的产率得到1-(α-D-arabinofuranosyl)-2-acetamidoimidazole
  参考文献：
  名称：

  Synthesis of Iodoaminoimidazole Arabinoside (IAIA): A Potential Reductive Metabolite of the Spect Imaging Agent, Iodoazomycin Arabinoside (IAZA)

  摘要：

  The stereospecific synthesis of 1-(5-deoxy-5-iodo-alpha-D-arabinofuranosyl)-2-aminoimidazole (iodoaminoimidazole arabinoside: IAIA, 2) is described. The reaction of the protected sugar bromide (8) and trifluoroacetamidoimidazole (10B) gave the coupled product (11B), which gave the free nucleoside (4) on deblocking. It was identical with AIA obtained by reduction of AZA (azomycin arabinoside), whose anomeric configuration was found to be a by the X-ray crystallography.

  DOI：

  10.1080/07328319908044860