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首页> 外文期刊>Chemistry: A European journal >Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism
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Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism

机译：用5-O-单丙基或5-改性核糖的核碱基直接糖基化合成核苷：改进的方案，范围和机制

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摘要

Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5- modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed "anhydrose") under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.
机译：由于其作为生物化学或抗癌和抗病毒剂的广泛用途，简化了对合成核苷的访问是有益的。 这里，通过用5-O- Tritylribose和其他C5-修饰的核糖衍生物的直接糖基化通过直接糖基化进入天然和合成核苷的膨胀范围的直接立体选择方法，从而通过直接糖基化和其他C5改性核糖衍生物。 反应通过在改性的Mitsunobu反应条件下形成1,2-anhydrosugar（称为“无水”）的原位的亲核环氧化物环。 描述了不同核苷和其他1取代的核苷衍生物的合成中的反应的范围。 另外，提供了对形成该关键糖基供体中间体的机械洞察。

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  • 来源
    《Chemistry: A European journal》 |2017年第16期|共8页
  • 作者

    A. Michael Downey; Radek Pohl; Jana Roithová; Michal Hocek;

  • 作者单位

    Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences Flemingovo nám. 2 16610 Prague 6 (Czech Republic);

    Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences Flemingovo nám. 2 16610 Prague 6 (Czech Republic);

    Department of Organic Chemistry Faculty of Science Charles University in Prague Hlavova 8 12843 Prague 2 (Czech Republic);

    Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences Flemingovo nám. 2 16610 Prague 6 (Czech Republic);

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 应用化学;
  • 关键词

    epoxides; glycosylation; nucleosides; riboses; synthesis design;

    机译：环氧化物;糖基化;核苷;核糖;合成设计;

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