[(2S)-5-(4-oxoimidazo[1,2-a][1,3,5]triazin-8-yl)oxolan-2-yl]methyl benzoate | 138840-86-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: [(2S)-5-(4-oxoimidazo[1,2-a][1,3,5]triazin-8-yl)oxolan-2-yl]methyl benzoate
• CAS: 138840-86-5；138921-20-7
• 化学式: C₁₇H₁₆N₄O₄
• 分子量: 340.338
• InChiKey: GVOJJUCHVFTVEJ-LSLKUGRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87.72
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [(2S)-5-(4-oxoimidazo[1,2-a][1,3,5]triazin-8-yl)oxolan-2-yl]methyl benzoate 在 氨 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以30%的产率得到8-(2,3-dideoxy-β-D-glycero-pentofuranosyl)imidazo<1,2-a>-s-triazin-4-one
  参考文献：
  名称：

  Novel dideoxynucleoside isosteres

  摘要：

  Novel 5-aza-7-deaza isosteres of the anti-HIV compounds, dideoxyinosine (ddI) and dideoxyguanosine (ddG), have been prepared by glycosylation of the corresponding isosteric bases with appropriately tailored dideoxyribose components. The glycosylation reactions were regiospecific and the position of glycosylation was established by UV and high-field NMR data. However, attempted preparation of the 3-deaza-5-aza isostere of dideoxyinosine led to a different regioisomer, a ring-extended dideoxycytidine analogue, whose structure was established by X-ray crystallographic data. The 5-aza-7-deaza isosteres of ddI and ddG were more stable with respect to hydrolytic cleavage than ddI and ddG.

  DOI：

  10.1016/s0040-4020(01)86501-7
• 作为产物：
  描述：

  5-O-benzoyl-2,3-dideoxy-D-glycero-pentofuranose 在 4-二甲氨基吡啶 三氟甲磺酸三甲基硅酯 、 牛血清白蛋白 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 [(2S)-5-(4-oxoimidazo[1,2-a][1,3,5]triazin-8-yl)oxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  Novel dideoxynucleoside isosteres

  摘要：

  Novel 5-aza-7-deaza isosteres of the anti-HIV compounds, dideoxyinosine (ddI) and dideoxyguanosine (ddG), have been prepared by glycosylation of the corresponding isosteric bases with appropriately tailored dideoxyribose components. The glycosylation reactions were regiospecific and the position of glycosylation was established by UV and high-field NMR data. However, attempted preparation of the 3-deaza-5-aza isostere of dideoxyinosine led to a different regioisomer, a ring-extended dideoxycytidine analogue, whose structure was established by X-ray crystallographic data. The 5-aza-7-deaza isosteres of ddI and ddG were more stable with respect to hydrolytic cleavage than ddI and ddG.

  DOI：

  10.1016/s0040-4020(01)86501-7