5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-5-methyluridine | 161824-93-7

• 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-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-5-methyluridine
• 英文别名: 1-[(2R,5S)-5-[(4-methoxyphenyl)methoxymethyl]-2,5-dihydrofuran-2-yl]-3-[(4-methoxyphenyl)methyl]-5-methylpyrimidine-2,4-dione
• CAS: 161824-93-7
• 化学式: C₂₆H₂₈N₂O₆
• 分子量: 464.518
• InChiKey: BVIQHGUMUNSEQP-BJKOFHAPSA-N

物化性质

• 沸点：
  620.6±65.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-5-methyluridine 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以68%的产率得到司他夫定
  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：

  5-甲基尿甙 在 咪唑 、 二氯乙酸 、 碘 、 sodium hydride 、 对甲苯磺酸 、 三苯基膦 作用下， 以 乙二醇二甲醚 、 1,2-二氯乙烷 、 甲苯 、 乙腈 为溶剂， 反应 23.16h， 生成 5'-O-(4-Methoxybenzyl)-2',3'-didehydro-2',3'-dideoxy-N³-(4-methoxybenzyl)-5-methyluridine
  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

文献信息

• A Facile Route to Pyrimidine-Based Nucleoside Olefins: Application to the Synthesis of d4T (Stavudine)
  作者：Frederick A. Luzzio、Michael E. Menes

  DOI：10.1021/jo00103a017

  日期：1994.12

  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.