rac-(1'S,2'S,3'S)-3'-(hydroxymethyl)-1',2',3',N-tetrahydroimidazo[1',3']-2''-aminooxazolo[1',2']-pyrimidine-4-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: rac-(1'S,2'S,3'S)-3'-(hydroxymethyl)-1',2',3',N-tetrahydroimidazo[1',3']-2''-aminooxazolo[1',2']-pyrimidine-4-carbonitrile
• 英文别名: (2R,6R,7S)-4-amino-7-(hydroxymethyl)-5-oxa-1,3,8,11-tetrazatricyclo[7.3.0.02,6]dodeca-3,9,11-triene-10-carbonitrile
• 化学式: C₉H₁₀N₆O₂
• 分子量: 234.217
• InChiKey: WKRNOQQWDVCWDY-BBVRLYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  羟乙醛 、 5-氨基-1H-咪唑-4-甲腈 、 2-氨基恶唑 以 water-d2 为溶剂， 反应 120.0h， 以60%的产率得到rac-(1'S,2'S,3'S)-3'-(hydroxymethyl)-1',2',3',N-tetrahydroimidazo[1',3']-2''-aminooxazolo[1',2']-pyrimidine-4-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.