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Regioselective synthesis of 5-[(2,3-dihydroxypropoxy)methyl]uracil analogues

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Abstract

Herein, we report the regioselective synthesis of 5-[(2,3-dihydroxypropoxy)methyl]uracil analogues with hydroxy alkyl chains that mimic the natural C-nucleoside pseudouridine. We developed multiple disparate synthetic procedures and approaches for the preparation of a wide range of derivatives, such as amino, acyl, halogen or azido compounds. Their synthesis was based on the different reactivity of the primary and secondary hydroxy groups. The final compounds might be further considered as new building blocks for oligonucleotide synthesis.

Graphical abstract: Regioselective synthesis of 5-[(2,3-dihydroxypropoxy)methyl]uracil analogues

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Publication details

The article was received on 14 Aug 2017, accepted on 06 Sep 2017 and first published on 07 Sep 2017


Article type: Paper
DOI: 10.1039/C7NJ03019C
Citation: New J. Chem., 2017, Advance Article
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    Regioselective synthesis of 5-[(2,3-dihydroxypropoxy)methyl]uracil analogues

    I. Mejdrová, L. Brulíková, T. Volná and J. Hlaváč, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ03019C

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