8-(β-D-2'-deoxy-3',5'-bis(4-toluoyloxy)ribofuranosyl)imidazo[1,2-a]-1,3,5-triazine-2(8H),4(3H)-dione | 357638-64-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 8-(β-D-2'-deoxy-3',5'-bis(4-toluoyloxy)ribofuranosyl)imidazo[1,2-a]-1,3,5-triazine-2(8H),4(3H)-dione
• 英文别名: [(2R,3S,5R)-5-(2,4-dioxoimidazo[1,2-a][1,3,5]triazin-8-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 357638-64-3
• 化学式: C₂₆H₂₄N₄O₇
• 分子量: 504.499
• InChiKey: JUBWXGOAULYURZ-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-(β-D-2'-deoxy-3',5'-bis(4-toluoyloxy)ribofuranosyl)imidazo[1,2-a]-1,3,5-triazine-2(8H),4(3H)-dione 在 氨 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以80%的产率得到8-(β-D-2'-deoxyribofuranosyl)imidazo[1,2-a]-1,3,5-triazine-2(8H),4(3H)-dione
  参考文献：
  名称：

  Fluorescent Charge-Neutral Analogue of Xanthosine:  Synthesis of a 2‘-Deoxyribonucleoside Bearing a 5-Aza-7-deazaxanthine Base

  摘要：

  A concise route is described to prepare the 5-aza-7-deazapurine 2 ' -deoxyriboside (4), which presents the puADA hydrogen-bonding pattern, analogous to the hydrogen-bonding pattern presented by 2 ' -deoxyxanthosine (2). The route begins with the commercially available 1-alpha -chloro-2-deoxy-3-5-bistoluoyloxyribofuranose (10), which proves to be a versatile point of entry to beta -2 ' -deoxyribofuranosides. In the first step, 2-nitroimidazole (8) is coupled with 10 to yield intermediate 11. Reduction of the nitro group to an amino group yields 12, which is treated with phenyl isocyanatoformate to complete the nucleobase to yield 13. Removal of the toluoyloxy protecting groups of 13 yields the target nucleoside 4 in 40% overall yield in four steps. In an alternative strategy, convergent coupling of 14 with 10 under basic conditions was attempted but found to yield the heterocycle glycosylated at the undesired position. Compound 13 displays potentially useful fluorescence properties. After excitation at 250 nm, a solution of 13 in MeCN shows a fluorescence emission with a maximum at 410 Dm. Furthermore, 13 is neutral at physiological pH, a property that it shares with natural nucleobases but not xanthosine itself, which is an acid with a pK(a) of ca. 5.6. Furthermore, as part of the design, 4 is made capable of presenting an unshared pair of electrons to the DNA minor groove.

  DOI：

  10.1021/jo005743h
• 作为产物：
  描述：

  1-(β-D-2'-deoxy-3',5'-bis(4-toluoyloxy)ribofuranosyl)-2-nitroimidazole 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 8-(β-D-2'-deoxy-3',5'-bis(4-toluoyloxy)ribofuranosyl)imidazo[1,2-a]-1,3,5-triazine-2(8H),4(3H)-dione
  参考文献：
  名称：

  Fluorescent Charge-Neutral Analogue of Xanthosine:  Synthesis of a 2‘-Deoxyribonucleoside Bearing a 5-Aza-7-deazaxanthine Base

  摘要：

  A concise route is described to prepare the 5-aza-7-deazapurine 2 ' -deoxyriboside (4), which presents the puADA hydrogen-bonding pattern, analogous to the hydrogen-bonding pattern presented by 2 ' -deoxyxanthosine (2). The route begins with the commercially available 1-alpha -chloro-2-deoxy-3-5-bistoluoyloxyribofuranose (10), which proves to be a versatile point of entry to beta -2 ' -deoxyribofuranosides. In the first step, 2-nitroimidazole (8) is coupled with 10 to yield intermediate 11. Reduction of the nitro group to an amino group yields 12, which is treated with phenyl isocyanatoformate to complete the nucleobase to yield 13. Removal of the toluoyloxy protecting groups of 13 yields the target nucleoside 4 in 40% overall yield in four steps. In an alternative strategy, convergent coupling of 14 with 10 under basic conditions was attempted but found to yield the heterocycle glycosylated at the undesired position. Compound 13 displays potentially useful fluorescence properties. After excitation at 250 nm, a solution of 13 in MeCN shows a fluorescence emission with a maximum at 410 Dm. Furthermore, 13 is neutral at physiological pH, a property that it shares with natural nucleobases but not xanthosine itself, which is an acid with a pK(a) of ca. 5.6. Furthermore, as part of the design, 4 is made capable of presenting an unshared pair of electrons to the DNA minor groove.

  DOI：

  10.1021/jo005743h