Synthesis and reactions of some uracil and 5-halouracil nucleosides of 2-acetamido-2-deoxy-D-glucose

Abstract

Silylated uracils react with 2-acetamido-1,3,4,6-tetra-Ο-acetyl-2-deoxy-D-glucose (5) under trimethylsilyl trifluoromethanesulfonate catalysis to give the nucleosides 6, 8, 10 and 12, respectively, as well as the diglycoside 14. Deblocking with sodium methoxide in methanol afforded the free nucleosides 7, 9, 11 and 13, respectively. Alternatively, the free nucleosides 11 and 13 were obtained directly by halogenation of 7 with N-bromosuccinimide or iodine monochloride, respectively. The structures of the synthesized compounds were confirmed by their 1H NMR, UV and mass spectra and elemental analyses. © Acta Chemica Scandinavica 1997.