Stereoselective synthesis of C-4′-aminouridines (uracil C-4-amino-D-ribonucleosides)

Abstract

The first C-4′-aminouridines can be synthesized in an α,β-stereoselective manner starting from L-glutamic acid. For the synthesis of α-C-4′-aminouridine, a key compound 9 is cyclized with trifluoroacetic acid followed by reduction with NaBH₃CN, while 9 is reduced with NaBH₄ followed by mesylation to give β-C-4′-aminouridine. Further, an acetonide-protection method is preferred for the synthesis of α-C-4′-aminouridine.