Propionic acid (2R,3R,4R,5R)-2-(6-dipropionylamino-purin-9-yl)-4-propionyloxy-5-propionyloxymethyl-tetrahydro-furan-3-yl ester | 863591-82-6

• 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: Propionic acid (2R,3R,4R,5R)-2-(6-dipropionylamino-purin-9-yl)-4-propionyloxy-5-propionyloxymethyl-tetrahydro-furan-3-yl ester
• CAS: 863591-82-6
• 化学式: C₂₅H₃₃N₅O₉
• 分子量: 547.565
• InChiKey: HIRDGYMXCJUSMJ-ALPMVPHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  169.11
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Propionic acid (2R,3R,4R,5R)-2-(6-dipropionylamino-purin-9-yl)-4-propionyloxy-5-propionyloxymethyl-tetrahydro-furan-3-yl ester 以 甲醇 为溶剂， 生成 Propionic acid (2R,3R,4R,5R)-2-(6-propionylamino-purin-9-yl)-4-propionyloxy-5-propionyloxymethyl-tetrahydro-furan-3-yl ester
  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 、 腺苷 在 吡啶 作用下， 生成 Propionic acid (2R,3R,4R,5R)-2-(6-propionylamino-purin-9-yl)-4-propionyloxy-5-propionyloxymethyl-tetrahydro-furan-3-yl ester 、 Propionic acid (2R,3R,4R,5R)-2-(6-dipropionylamino-purin-9-yl)-4-propionyloxy-5-propionyloxymethyl-tetrahydro-furan-3-yl ester
  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