5'-O-Benzyl-2',3'-didehydro-2',3'-dideoxy-N³-benzyluridine | 161824-91-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 5'-O-Benzyl-2',3'-didehydro-2',3'-dideoxy-N³-benzyluridine
• 英文别名: 3-benzyl-1-[(2R,5S)-5-(phenylmethoxymethyl)-2,5-dihydrofuran-2-yl]pyrimidine-2,4-dione
• CAS: 161824-91-5
• 化学式: C₂₃H₂₂N₂O₄
• 分子量: 390.439
• InChiKey: PFGSCVSVDCBHMD-RBBKRZOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5'-O-Benzyl-2',3'-didehydro-2',3'-dideoxy-N³-benzyluridine 在 platinum on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以96%的产率得到5'-O-Benzyl-2',3'-dideoxy-N³-benzyluridine
  参考文献：
  名称：

  A Facile Route to Pyrimidine-Based Nucleoside Olefins: Application to the Synthesis of d4T (Stavudine)

  摘要：

  An efficient synthetic route to nucleoside olefins in the uridine, cytidine, and thymidine series is described which utilizes the Garegg-Samuelsson iodine/triphenylphosphine/imidazole-promoted deoxygenation of the 2',3'-hydroxyl groups as the key step. Cyclopentylidene ketal protection was employed for all the nucleoside 2',3'-hydroxyls to facilitate blocking of the 5'-hydroxyl and the pyrimidine nitrogens with the benzyl or 4-methoxybenzyl (PMB) groups. Deblocking of the cyclopentylidene group followed by olefination of the resulting diols provided protected nucleoside olefins 18-20. Starting with 5-methyluridine 4 and utilizing the 4-methoxybenzyl group for 5',N-3 protection, the overall scheme provided the anti-HIV compound d4T (1) after deprotection of the PMB groups. The dibenzylhypoxanthine nucleoside diol 17 derived from inosine gave either unreacted starting material or decomposition products under several sets of conditions.

  DOI：

  10.1021/jo00103a017
• 作为产物：
  描述：

  1-(2',3'-Dihydroxy-5'-O-benzyl-β-D-erythro-pentofuranosyl)-N³-benzyluracil 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 10.0h， 以87%的产率得到5'-O-Benzyl-2',3'-didehydro-2',3'-dideoxy-N³-benzyluridine
  参考文献：
  名称：

  A Facile Route to Pyrimidine-Based Nucleoside Olefins: Application to the Synthesis of d4T (Stavudine)

  摘要：

  An efficient synthetic route to nucleoside olefins in the uridine, cytidine, and thymidine series is described which utilizes the Garegg-Samuelsson iodine/triphenylphosphine/imidazole-promoted deoxygenation of the 2',3'-hydroxyl groups as the key step. Cyclopentylidene ketal protection was employed for all the nucleoside 2',3'-hydroxyls to facilitate blocking of the 5'-hydroxyl and the pyrimidine nitrogens with the benzyl or 4-methoxybenzyl (PMB) groups. Deblocking of the cyclopentylidene group followed by olefination of the resulting diols provided protected nucleoside olefins 18-20. Starting with 5-methyluridine 4 and utilizing the 4-methoxybenzyl group for 5',N-3 protection, the overall scheme provided the anti-HIV compound d4T (1) after deprotection of the PMB groups. The dibenzylhypoxanthine nucleoside diol 17 derived from inosine gave either unreacted starting material or decomposition products under several sets of conditions.

  DOI：

  10.1021/jo00103a017