methyl (2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-ylcarbamate | 123533-08-4

• 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: methyl (2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-ylcarbamate
• 英文别名: 3'-methylcarbamate-3'-deoxythymidine；methyl N-[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-3-yl]carbamate；methyl N-[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]carbamate
• CAS: 123533-08-4
• 化学式: C₁₂H₁₇N₃O₆
• 分子量: 299.283
• InChiKey: RLHOKMJCGDHYQA-DJLDLDEBSA-N

物化性质

• 熔点：
  102-105 °C(Solv: acetonitrile (75-05-8))
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  beta-胸苷 在 palladium on activated charcoal sodium azide 、 Dowex 50(H+) 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 methyl (2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-ylcarbamate
  参考文献：
  名称：

  3'-取代-2'，3'-二脱氧核苷类似物的合成作为潜在的抗抑郁药

  摘要：

  3'-氨基-3'-脱氧胸苷分六个步骤制备，胸腺嘧啶核苷的总收率为67％。五个衍生品和复合他们的抗HIV活性进行了测试。

  DOI：

  10.1016/s0040-4039(00)99623-0

文献信息

• Straightforward carbamoylation of nucleophilic compounds employing organic azides, phosphines, and aqueous trialkylammonium hydrogen carbonate
  作者：Andrey Yagodkin、Kerstin Löschcke、Janne Weisell、Alex Azhayev

  DOI：10.1016/j.tet.2010.01.017

  日期：2010.3

  the intermediate formation of the corresponding isocyanate, which, in turn, reacts further with a nucleophilic reagent also present in the mixture and results in carbamoylation with good yield. On the basis of this reaction a practical carbamoylation procedure was devised and a comparative study on suitability of different solvents and phosphorus (III) derivatives for carbamoylation reaction was conducted

  在碳酸氢三烷基铵水溶液的存在下，施陶丁格反应导致相应异氰酸酯的中间形成，该异氰酸酯又与混合物中也存在的亲核试剂进一步反应，并以高收率进行氨基甲酰化反应。在此反应的基础上，设计了一种实用的氨基甲酰化方法，并进行了对比研究，研究了不同溶剂和磷（III）衍生物对氨基甲酸酯化反应的适用性。该方法的多功能性通过不同类别的亲核化合物（包括氨基甲基树脂和在有机溶剂中显示不良溶解性的天然化合物）的实例得到证明。
• Synthesis and evaluation of new 2′,3′-dideoxynucleoside analogs as potential anti-AIDS and anti-herpes drugs
  作者：A Faraj、M Maillard、M Lemaître、S Letellier、F Frappier、JC Florent、DS Grierson、C Monneret、A Zerial

  DOI：10.1016/0223-5234(92)90102-7

  日期：1992.3

  Based on the known structure-activity relationships for the active anti-HIV, a series of 3'-deoxy-3'-N-functionalized thymidine analogs has been synthesized from thymidine. Evaluation for inhibitory activity against human immunodeficiency virus (HIV) replication in CEM cells and against herpes simplex virus in MRC-5 cells is reported.
• Synthesis of 3′-substituted-2′,3′-dideoxynucleoside analogs as potential anti-aids drugs
  作者：Michel Maillard、Abdesslem Faraj、François Frappier、Jean-Claude Florent、David S. Grierson、Claude Monneret

  DOI：10.1016/s0040-4039(00)99623-0

  日期：1989.1

  3′-Amino-3′-deoxythymidine was prepared in six steps and in 67% overall yield from thymidine. Five derivatives of and compound were tested for their anti-HIV activity.

  3'-氨基-3'-脱氧胸苷分六个步骤制备，胸腺嘧啶核苷的总收率为67％。五个衍生品和复合他们的抗HIV活性进行了测试。