3-<2-phenyl-4-(2,3-O-isopropylidene-β-D-ribofuranosyl)imidazolyl>-2-oxo-1-propanol | 133535-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-<2-phenyl-4-(2,3-O-isopropylidene-β-D-ribofuranosyl)imidazolyl>-2-oxo-1-propanol
• 英文别名: 1-[4-[(3aS,4S,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-phenyl-1H-imidazol-5-yl]-3-hydroxypropan-2-one
• CAS: 133535-95-2
• 化学式: C₂₀H₂₄N₂O₆
• 分子量: 388.42
• InChiKey: LLIAOSYGVQWGEV-NRSFXHEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113.9
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  3-<2-phenyl-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazolyl>-2-oxo-1-propanol 在 sodium hydroxide 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 14.5h， 生成 3-<2-phenyl-4-(2,3-O-isopropylidene-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：——