2',3',5'-tri-O-isobutyryladenosine | 863591-89-3

• 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',3',5'-tri-O-isobutyryladenosine
• 英文别名: isobutyric acid (2R,3R,4R,5R)-2-(6-amino-purin-9-yl)-4-isobutyryloxy-5-isobutyryloxymethyl-tetrahydro-furan-3-yl ester；isobutyryl(-2)[isobutyryl(-3)][isobutyryl(-5)]Ribf(b)-adenin-9-yl；[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-bis(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate
• CAS: 863591-89-3
• 化学式: C₂₂H₃₁N₅O₇
• 分子量: 477.517
• InChiKey: HAGJQJVFPPELEJ-NVQRDWNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-isobutyryladenosine 在 正丁基锂 、 2,2,2-三氟乙醇 作用下， 以 正己烷 为溶剂， 反应 1.0h， 以64%的产率得到5'-O-isobutyryladenosine
  参考文献：
  名称：

  Selective Removal of the 2‘- and 3‘-O-Acyl Groups from 2‘,3‘,5‘-Tri-O-acylribonucleoside Derivatives with Lithium Trifluoroethoxide¹

  摘要：

  Selective cleavage of O2' and O3' ester groups from ribonucleoside derivatives has been accomplished with Dowex 1 x 2 (CF3CH2O-) in 2,2,2-trifluoroethanol (TFE) or lithium trifluoroethoxide/TFE. Deacylations with Li+ -OCH2CF3/TFE proceed at ambient temperature (or with mild heating) to give the 5'-O-acyl derivatives in superior yields and higher purity than prior approaches for selective O2' and O3' ester deprotection.

  DOI：

  10.1021/jo0600104
• 作为产物：
  描述：

  6-N,N-dibenzoyl-2',3',5'-tri-O-isobutyryladenosine 以 甲醇 为溶剂， 反应 12.0h， 以88%的产率得到2',3',5'-tri-O-isobutyryladenosine
  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

• 糖环修饰的核苷类似物、制备方法及其在制备具有抗疲劳功能产品中的应用
  申请人：中国人民解放军军事科学院军事医学研究院

  公开号：CN113813280A

  公开（公告）日：2021-12-21

  本发明涉及制药技术领域，具体涉及糖环修饰的核苷类似物、制备方法及其在制备具有抗疲劳功能产品中的应用。本发明首次发现了，多种现有的AICAR类似物和腺苷类似物也能够用于提升体能，发挥抗疲劳功能。本发明还进一步合成了多种新的AICAR类似物和腺苷类似物，并提供了含有上述AICAR类似物和/或腺苷类似物的药物，给出了所述药物在应用时的有效剂量为0.0094～4.7mmol/kg/d。
• 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.
• Selective Removal of the 2‘- and 3‘-<i>O</i>-Acyl Groups from 2‘,3‘,5‘-Tri-<i>O</i>-acylribonucleoside Derivatives with Lithium Trifluoroethoxide¹
  作者：Ireneusz Nowak、Carl T. Jones、Morris J. Robins

  DOI：10.1021/jo0600104

  日期：2006.4.1

  Selective cleavage of O2' and O3' ester groups from ribonucleoside derivatives has been accomplished with Dowex 1 x 2 (CF3CH2O-) in 2,2,2-trifluoroethanol (TFE) or lithium trifluoroethoxide/TFE. Deacylations with Li+ -OCH2CF3/TFE proceed at ambient temperature (or with mild heating) to give the 5'-O-acyl derivatives in superior yields and higher purity than prior approaches for selective O2' and O3' ester deprotection.