Zelli Renaud, Zeinyeh Waël, Décout Jean-Luc
Université Grenoble Alpes, CNRS, DPM, Grenoble, France.
Université Grenoble Alpes, CNRS, CEA, BIG-LCBM, Grenoble, France.
Curr Protoc Nucleic Acid Chem. 2018 Sep;74(1):e57. doi: 10.1002/cpnc.57. Epub 2018 Aug 13.
A one-pot glycosylation and cyclization procedure is described for the synthesis of 6-chloropurine ribonucleosides from chloropyrimidines. From such a procedure and modification of the obtained chloropurine ribonucleosides, many drug candidates or molecular tools for biological study designed from their similarity to naturally occurring nucleosides could be obtained. The synthesis begins by preparation of several amidinoaminochloropyrimidines as precursors for the one-pot procedure. Then, by adding trimethylsilyl trifluoromethanesulfonate (TMSOTf) to a mixture of a pyrimidine and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribose, different 6-chloropurine ribonucleosides are obtained. This methodology allows the straightforward introduction of an alkyl substituent at position 8 of purine ribonucleosides, which then can be functionalized at positions 2 and 6. © 2018 by John Wiley & Sons, Inc.
描述了一种用于从氯嘧啶合成6-氯嘌呤核糖核苷的一锅法糖基化和环化方法。通过这样的方法以及对所得氯嘌呤核糖核苷的修饰，可以获得许多基于与天然核苷相似性而设计的生物研究候选药物或分子工具。合成首先制备几种脒基氨基氯嘧啶作为一锅法的前体。然后，通过向嘧啶和1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-核糖的混合物中加入三甲基甲硅烷基三氟甲磺酸酯（TMSOTf），得到不同的6-氯嘌呤核糖核苷。这种方法允许在嘌呤核糖核苷的8位直接引入烷基取代基，然后该取代基可以在2位和6位进行官能化。©2018约翰威立父子公司版权所有
