Synthesis of 5-(2-amino-2-deoxy-β- -glucopyranosyloxymethyl)-2′-deoxyuridine and its incorporation into oligothymidylates

The protected 5-(2-amino-2-deoxy-β- -glucopyranosyloxymethyl)-2′-deoxyuridine phosphoramidite 15 has been prepared from uridine in 12 steps. When incorporated into oligodeoxyribonucleotides the novel nucleoside analog 5 leads to decreased binding affinity. This decrease is larger with a complementary RNA-strand than with a DNA complement.