1-(alpha-D-阿拉伯呋喃糖基)-1H-咪唑-2-胺 | 250693-28-8

• 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
• 中文名称: 1-(alpha-D-阿拉伯呋喃糖基)-1H-咪唑-2-胺
• 英文名称: 1-(α-D-arabinofuranosyl)-2-aminoimidazole
• 英文别名: (2S,3S,4S,5R)-2-(2-Amino-1H-imidazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol；(2S,3S,4S,5R)-2-(2-aminoimidazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 250693-28-8
• 化学式: C₈H₁₃N₃O₄
• 分子量: 215.209
• InChiKey: ICTIXDHPYOICMN-JWXFUTCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  114
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(alpha-D-阿拉伯呋喃糖基)-1H-咪唑-2-胺 在 碘 、 三苯基膦 作用下， 以 吡啶 为溶剂， 反应 2.0h， 以40%的产率得到1-(5-deoxy-5-iodo-α-D-arabinofuranosyl)-2-aminoimidazole
  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：

  methyl tri-O-benzoyl-α-D-arabinofuranoside 在 氢氧化钾 、 氨 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 70.0h， 生成 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

文献信息

• Synthesis of Iodoaminoimidazole Arabinoside (IAIA): A Potential Reductive Metabolite of the Spect Imaging Agent, Iodoazomycin Arabinoside (IAZA)
  作者：Herbert C. Lee、Piyush Kumar、Leonard I. Wiebe、Robert McDonald、John R. Mercer、Kazue Ohkura、Koh-Ichi Seki

  DOI：10.1080/07328319908044860

  日期：1999.9

  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.