4-N-2',3',5'-tri-O-tetrapropionylcytidine | 31448-50-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-N-2',3',5'-tri-O-tetrapropionylcytidine
• 英文别名: N⁴,O^2'_,O3'_,O5'-tetrapropionyl-cytidine；[(2R,3R,4R,5R)-5-[2-oxo-4-(propanoylamino)pyrimidin-1-yl]-3,4-di(propanoyloxy)oxolan-2-yl]methyl propanoate
• CAS: 31448-50-7
• 化学式: C₂₁H₂₉N₃O₉
• 分子量: 467.476
• InChiKey: IARFAUXXBUGAOL-AJSUPXSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-N-2',3',5'-tri-O-tetrapropionylcytidine 以 甲醇 为溶剂， 反应 3.0h， 以77%的产率得到2',3',5'-tri-O-propionylcytidine
  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：

  丙酸酐 、 胞苷 在 吡啶 作用下， 反应 2.0h， 生成 4-N-2',3',5'-tri-O-tetrapropionylcytidine
  参考文献：
  名称：

  Hydrothermal Deamidation of 4-N-Acylcytosine Nucleoside Derivatives:  Efficient Synthesis of Uracil Nucleoside Esters

  摘要：

  [GRAPHICS]N,O-Peracylated cytidine and 2'-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125 degrees C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.

  DOI：

  10.1021/ol0518378

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.
• Hydrothermal Deamidation of 4-<i>N</i>-Acylcytosine Nucleoside Derivatives:  Efficient Synthesis of Uracil Nucleoside Esters
  作者：Ireneusz Nowak、Morris J. Robins

  DOI：10.1021/ol0518378

  日期：2005.10.1

  [GRAPHICS]N,O-Peracylated cytidine and 2'-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125 degrees C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.