Regioselective synthesis of 5-[(2,3-dihydroxypropoxy)methyl]uracil analoguesElectronic supplementary information (ESI) available. See DOI: 10.1039/c7nj03019c

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. The regioselective synthesis of dihydroxypropoxymethyluracil analogues with hydroxy alkyl chains that mimic the natural C-nucleoside pseudouridine is reported.