4-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((R)-1,2-dihydroxyethyl)-3-hydroxy-1,2,3,4-tetrahydroimidazo[1,5-a]-pyrimidine-8-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((R)-1,2-dihydroxyethyl)-3-hydroxy-1,2,3,4-tetrahydroimidazo[1,5-a]-pyrimidine-8-carbonitrile
• 英文别名: (2R,3S,4S)-4-(4-amino-2-oxopyrimidin-1-yl)-2-[(1R)-1,2-dihydroxyethyl]-3-hydroxy-1,2,3,4-tetrahydroimidazo[1,5-a]pyrimidine-8-carbonitrile
• 化学式: C₁₃H₁₅N₇O₄
• 分子量: 333.307
• InChiKey: JCEKJPQSKJMTIA-UWGFBGMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  173
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  丙炔腈 、 rac-3'-(4',5'-dihydroxyethyl)-1',2',3',N-tetrahydroimidazo[1',3']-2''-aminooxazolo[1',2']-pyrimidine-4-carbonitrile 以 水 为溶剂， 反应 24.0h， 以82%的产率得到4-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-((R)-1,2-dihydroxyethyl)-3-hydroxy-1,2,3,4-tetrahydroimidazo[1,5-a]-pyrimidine-8-carbonitrile
  参考文献：
  名称：

  Chemoselective Multicomponent One-Pot Assembly of Purine Precursors in Water

  摘要：

  The recent development of a sequential, high-yielding route to activated pyrimidine nucleotides, under conditions thought to be prebiotic, is an encouraging step toward the greater goal of a plausible prebiotic pathway to RNA and the potential for an RNA world. However, this synthesis has led to a disparity in the methodology available for stepwise construction of the canonical pyrimidine and purine nucleotides. To address this problem, and further explore prebiotically accessible chemical systems, we have developed a high-yielding, aqueous, one-pot, multicomponent reaction that tethers masked-sugar moieties to prebiotically plausible purine precursors. A pH-dependent three-component reaction system has been discovered that utilizes key nucleotide synthons 2-aminooxazole and 5-aminoimidazoles, which allows the first divergent purine/pyrimidine synthesis to be proposed. Due to regiospecific aminoimidazole tethering, the pathway allows N9 purination only, thus suggesting the first prebiotically plausible mechanism for regiospecific N9 purination.

  DOI：

  10.1021/ja108197s

文献信息

• Chemoselective Multicomponent One-Pot Assembly of Purine Precursors in Water
  作者：Matthew W. Powner、John D. Sutherland、Jack W. Szostak

  DOI：10.1021/ja108197s

  日期：2010.11.24

  The recent development of a sequential, high-yielding route to activated pyrimidine nucleotides, under conditions thought to be prebiotic, is an encouraging step toward the greater goal of a plausible prebiotic pathway to RNA and the potential for an RNA world. However, this synthesis has led to a disparity in the methodology available for stepwise construction of the canonical pyrimidine and purine nucleotides. To address this problem, and further explore prebiotically accessible chemical systems, we have developed a high-yielding, aqueous, one-pot, multicomponent reaction that tethers masked-sugar moieties to prebiotically plausible purine precursors. A pH-dependent three-component reaction system has been discovered that utilizes key nucleotide synthons 2-aminooxazole and 5-aminoimidazoles, which allows the first divergent purine/pyrimidine synthesis to be proposed. Due to regiospecific aminoimidazole tethering, the pathway allows N9 purination only, thus suggesting the first prebiotically plausible mechanism for regiospecific N9 purination.