3-<2-methyl-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazolyl>-2-oxo-1-propanol | 133535-93-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-<2-methyl-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazolyl>-2-oxo-1-propanol
• 英文别名: [(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-[5-(3-hydroxy-2-oxopropyl)-2-methyl-1H-imidazol-4-yl]oxolan-2-yl]methyl benzoate
• CAS: 133535-93-0
• 化学式: C₃₃H₃₀N₂O₉
• 分子量: 598.609
• InChiKey: DEWJONNJFJHKLM-BQEQVSEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  154.11
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3(2H,6H)-one 、 乙酸乙脒 在 sodium carbonate 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以10%的产率得到3-<2-methyl-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazolyl>-2-oxo-1-propanol
  参考文献：
  名称：

  C-Nucleosides. 15. Novel Ring Transformation of 6-Hydroxy-6-(2,3,5-tri-O-benzoyl-b-D-ribofuranosyl)-2,6-dihydropyran-3-one with Amidines to Imidazole

  摘要：

  The novel ring transformation of 6-hydroxy-6-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dihydropyran-3-one (1) with amidines to imidazole is described. Treatment of 1 with benzamidine afforded 3-[2-phenyl-4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)imidazolyl]-2-oxo-1-propanol (2) in 53% yield. H-1 and C-13 nmr spectra of 2 accounted for the contribution of tautomeric structure. Deprotection of 2 with methanolic sodium hydroxide afforded 3-[2-phenyl-4-(beta-D-ribofuranosyl)imidazolyl]-2-oxo-1-propanol (5) in 35% yield. Treatment of 1 with O-methylisourea afforded 2-methoxyimidazole (3) in 27% yield. Treatment of 1 with acetamidine afforded 2-methylimidazole (4) in 10% yield. However, debenzoylation of 3 and 4 with alkaline did not afforded the deprotected imidazole C-nucleosides.

  DOI：

  10.3987/com-90-5615

文献信息

• MAEBA, ISAMU;OSAKA, KAZUYA;ITO, CHIHIRO, HETEROCYCLES, 31,(1990) N2, C. 2225-2230
  作者：MAEBA, ISAMU、OSAKA, KAZUYA、ITO, CHIHIRO

  DOI：——

  日期：——