[4-13C]-(2R,3R,4S,5R)-5-(2-acetamido-6-chloro-9H-purin-9-yl)-2-(acetoxymethyl)-4-hydroxy-4-trideuteromethyltetrahydrofuran-3-yl acetate | 1350981-79-1

• 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: [4-13C]-(2R,3R,4S,5R)-5-(2-acetamido-6-chloro-9H-purin-9-yl)-2-(acetoxymethyl)-4-hydroxy-4-trideuteromethyltetrahydrofuran-3-yl acetate
• 英文别名: [4-¹³C]-(2R,3R,4S,5R)-5-(2-acetamido-6-chloro-9H-purin-9-yl)-2-(acetoxymethyl)-4-hydroxy-4-trideuteromethyltetrahydrofuran-3-yl acetate
• CAS: 1350981-79-1
• 化学式: C₁₇H₂₀ClN₅O₇
• 分子量: 445.793
• InChiKey: RSJXLQWHDQYOAW-XRKWTMRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  154.76
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  [4-13C]-(2R,3R,4S,5R)-5-(2-acetamido-6-chloro-9H-purin-9-yl)-2-(acetoxymethyl)-4-hydroxy-4-trideuteromethyltetrahydrofuran-3-yl acetate 在 二甲氨基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以0.21 g的产率得到[4-¹³C]-(2R,3R,4R,5R)-5-(2-acetamido-6-chloro-9H-purin-9-yl)-2-(acetoxymethyl)-4-fluoro-4-trideuteromethyltetrahydrofuran-3-yl acetate
  参考文献：
  名称：

  Synthesis of Stable Isotope Labeled Analogs of the Anti-Hepatitis C Virus Nucleotide Prodrugs PSI-7977 and PSI-352938

  摘要：

  In order to support bioanalytical LC/MS method development and plasma sample analysis in preclinical and clinical studies of the anti-hepatitis C-virus nucleotides, PSI-7977 and PSI-352938, the corresponding stable isotope labeled forms were prepared. These labeled compounds were prepared by addition reaction of the freshly prepared Grignard reagent (CD3MgI)-C-13 to the corresponding 2'-ketone nucleosides followed by fluorination of the resulting carbinol with DAST. As expected, these 2'-C-(trideuterated-C-13-methyl) nucleotide prodrugs showed similar anti-HCV activity to that of the corresponding unlabeled ones.

  DOI：

  10.1080/15257770.2011.614308
• 作为产物：
  描述：

  N-(6-chloro-9-((6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-9H-purin-2-yl)acetamide 在 吡啶 、 aluminum (III) chloride 、 magnesium 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 [4-13C]-(2R,3R,4S,5R)-5-(2-acetamido-6-chloro-9H-purin-9-yl)-2-(acetoxymethyl)-4-hydroxy-4-trideuteromethyltetrahydrofuran-3-yl acetate
  参考文献：
  名称：

  Synthesis of Stable Isotope Labeled Analogs of the Anti-Hepatitis C Virus Nucleotide Prodrugs PSI-7977 and PSI-352938

  摘要：

  In order to support bioanalytical LC/MS method development and plasma sample analysis in preclinical and clinical studies of the anti-hepatitis C-virus nucleotides, PSI-7977 and PSI-352938, the corresponding stable isotope labeled forms were prepared. These labeled compounds were prepared by addition reaction of the freshly prepared Grignard reagent (CD3MgI)-C-13 to the corresponding 2'-ketone nucleosides followed by fluorination of the resulting carbinol with DAST. As expected, these 2'-C-(trideuterated-C-13-methyl) nucleotide prodrugs showed similar anti-HCV activity to that of the corresponding unlabeled ones.

  DOI：

  10.1080/15257770.2011.614308