[2-(15)NH2]-2',3',5'-tri-O-acetyl-2-N-isobutyrylguanosine | 1234320-08-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: [2-(15)NH2]-2',3',5'-tri-O-acetyl-2-N-isobutyrylguanosine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2-(2-methylpropanoyl(15N)amino)-6-oxo-1H-purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 1234320-08-1
• 化学式: C₂₀H₂₅N₅O₉
• 分子量: 480.44
• InChiKey: YQSNJEPVDDEJNE-RZCXJJJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  177
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  [2-(15)NH2]-2',3',5'-tri-O-acetyl-6-O-benzyl-2-N-isobutyrylguanosine 在 palladium on carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以95%的产率得到[2-(15)NH2]-2',3',5'-tri-O-acetyl-2-N-isobutyrylguanosine
  参考文献：
  名称：

  ¹⁵N Double-Labeled Guanosine from Inosine through Ring-Opening−Ring-Closing and One-Pot Pd-Catalyzed C−O and C−N Cross-Coupling Reactions

  摘要：

  [N,1-N-15(2)]-Guanosine, or [1,NH2-N-15(2)]-guanosine, and derivatives were prepared from tri-O-acetylinosine, via N-nitration and reaction with (NH2OH)-N-15, followed by conversion of the N-15-labeled 1-hydroxyinosine to the corresponding 2,6-dichloropurine riboside. The sequential one-pot C-O and C-N key couplings of this dichloro derivative with PhCH2OH and (PhCONH2)-N-15 or (PrCONH2)-Pr-i-N-15 was achieved in good overall yields, with Pd(0)-Xantphos as the best choice of five different catalytic systems examined.

  DOI：

  10.1021/jo100808w