Issue 20, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
14 Aug 2017
Accepted
06 Sep 2017
First published
07 Sep 2017

New J. Chem., 2017,41, 12178-12189

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

I. Mejdrová, L. Brulíková, T. Volná and J. Hlaváč, New J. Chem., 2017, 41, 12178 DOI: 10.1039/C7NJ03019C

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