7-N-2',3',5'-tri-O-tetraacetylformycin | 13351-66-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-N-2',3',5'-tri-O-tetraacetylformycin
• 英文别名: Tetraacetyl formycin；(1S)-tri-O-acetyl-1-(7-acetylamino-1(2)H-pyrazolo[4,3-d]pyrimidin-3-yl)-D-1,4-anhydro-ribitol；[(2R,3R,4S,5S)-5-(7-acetamido-2H-pyrazolo[4,3-d]pyrimidin-3-yl)-3,4-diacetyloxyoxolan-2-yl]methyl acetate
• CAS: 13351-66-1
• 化学式: C₁₈H₂₁N₅O₈
• 分子量: 435.393
• InChiKey: BEZIBQDJYRIKGG-KLWIRTJPSA-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：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  172
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  7-N-2',3',5'-tri-O-tetraacetylformycin 以 甲醇 为溶剂， 反应 3.0h， 以84%的产率得到2',3',5'-tri-O-acetyl formycin
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 127. Selective N-Deacylation of N,O-Peracylated Nucleosides in Superheated Methanol¹

  摘要：

  Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath >= 105 degrees C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.

  DOI：

  10.1021/jo051256w
• 作为产物：
  描述：

  乙酸酐 、 formycin 在 吡啶 作用下， 反应 1.0h， 以100%的产率得到7-N-2',3',5'-tri-O-tetraacetylformycin
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 127. Selective N-Deacylation of N,O-Peracylated Nucleosides in Superheated Methanol¹

  摘要：

  Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath >= 105 degrees C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.

  DOI：

  10.1021/jo051256w

文献信息

• Nucleic Acid Related Compounds. 127. Selective N-Deacylation of N,O-Peracylated Nucleosides in Superheated Methanol¹
  作者：Ireneusz Nowak、Martin Conda-Sheridan、Morris J. Robins

  DOI：10.1021/jo051256w

  日期：2005.9.1

  Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath >= 105 degrees C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.