N-[9-[(3R,6S,7aS)-5-oxo-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-6-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide | 1311407-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N-[9-[(3R,6S,7aS)-5-oxo-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-6-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 1311407-03-0
• 化学式: C₂₁H₂₂N₆O₄
• 分子量: 422.443
• InChiKey: FPBTXTNWMARMAX-PJSUUKDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[9-[(3R,6S,7aS)-5-oxo-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-6-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide 在 甲醇 、 氨 作用下， 反应 60.0h， 以94%的产率得到(3R,6S,7aS)-6-(2-amino-6-oxo-1H-purin-9-yl)-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-5-one
  参考文献：
  名称：

  Synthesis of 3-Guaninyl- and 3-Adeninyl-5-hydroxymethyl-2-pyrrolidinone Nucleosides

  摘要：

  L- And D-glutamic acids, as well as trans-4-hydroxy-L-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.

  DOI：

  10.1021/jo2004617
• 作为产物：
  描述：

  鸟嘌呤 在 吡啶 、 4-二甲氨基吡啶 、 对硝基苯甲醇 、 偶氮二甲酸二异丙酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 N-[9-[(3R,6S,7aS)-5-oxo-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-6-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
  参考文献：
  名称：

  Synthesis of 3-Guaninyl- and 3-Adeninyl-5-hydroxymethyl-2-pyrrolidinone Nucleosides

  摘要：

  L- And D-glutamic acids, as well as trans-4-hydroxy-L-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.

  DOI：

  10.1021/jo2004617

文献信息

• Synthesis of 3-Guaninyl- and 3-Adeninyl-5-hydroxymethyl-2-pyrrolidinone Nucleosides
  作者：Abdullah Saleh、John G. D’Angelo、Martha D. Morton、Jesse Quinn、Kendra Redden、Rafal W. Mielguz、Christopher Pavlik、Michael B. Smith

  DOI：10.1021/jo2004617

  日期：2011.7.15

  L- And D-glutamic acids, as well as trans-4-hydroxy-L-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.