1-(2',3'-Dihydroxy-5'-O-benzyl-β-D-erythro-pentofuranosyl)-N³-benzyluracil | 161824-87-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(2',3'-Dihydroxy-5'-O-benzyl-β-D-erythro-pentofuranosyl)-N³-benzyluracil
• 英文别名: 3,5'-dibenzyluridine；1-Benzyl-5'-O-benzyluridin；3,O^5'-dibenzyl-uridine；3-benzyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phenylmethoxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 161824-87-9
• 化学式: C₂₃H₂₄N₂O₆
• 分子量: 424.453
• InChiKey: OBXJYHQEYZYNQX-ZHHKINOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  99.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  尿嘧啶核苷 在 sodium hydride 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 11.0h， 生成 1-(2',3'-Dihydroxy-5'-O-benzyl-β-D-erythro-pentofuranosyl)-N³-benzyluracil
  参考文献：
  名称：

  氟化尿苷类似物的合成和构象分析提供了对邻组参与机制的洞察

  摘要：

  氟化核苷类似物作为抗癌剂和抗病毒剂以及作为酶促功能的探针引起了很多关注。然而，缺乏直接合成方法，特别是对于 2',3'-双脱氧-2',3'-二氟核苷，阻碍了它们的实际应用。为了设计更有效的合成方法，更好地了解这些分子的构象和形成机制很重要。在此，我们报告了 2',3'-dideoxy-2',3'-difluoro 和 2'-deoxy-2'-fluorouridine 衍生物的合成和构象分析，并提供了对反应机制的深入了解。我们建议转换最有可能与 SN1 或 SN2 路径不同，而是通过相邻组参与机制进行操作。

  DOI：

  10.3390/molecules25235513

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.
• Synthesis and Conformational Analysis of Fluorinated Uridine Analogues Provide Insight into a Neighbouring-Group Participation Mechanism
  作者：Freideriki Michailidou、Tomas Lebl、Alexandra M. Z. Slawin、Sunil Vishnuprasadji Sharma、Murray J. B. Brown、Rebecca Jane Miriam Goss

  DOI：10.3390/molecules25235513

  日期：——

  methods, especially for 2′,3′-dideoxy-2′,3′-difluoro nucleosides, hamper their practical utility. In order to design more efficient synthetic methods, a better understanding of the conformation and mechanism of formation of these molecules is important. Herein, we report the synthesis and conformational analysis of a 2′,3′-dideoxy-2′,3′-difluoro and a 2′-deoxy-2′-fluoro uridine derivative and provide

  氟化核苷类似物作为抗癌剂和抗病毒剂以及作为酶促功能的探针引起了很多关注。然而，缺乏直接合成方法，特别是对于 2',3'-双脱氧-2',3'-二氟核苷，阻碍了它们的实际应用。为了设计更有效的合成方法，更好地了解这些分子的构象和形成机制很重要。在此，我们报告了 2',3'-dideoxy-2',3'-difluoro 和 2'-deoxy-2'-fluorouridine 衍生物的合成和构象分析，并提供了对反应机制的深入了解。我们建议转换最有可能与 SN1 或 SN2 路径不同，而是通过相邻组参与机制进行操作。