Uridine, 3'-azido-2',3'-dideoxy-5'-O-(triphenylmethyl)- → Navuridine

Participants

Reaction Steps

A mixture of 3'-azido-5'-O-trityl-2',3'-dideoxyuridine (63 g, 0.132 mol) and 300 ml of acetic acid (80%) was heated at 95°-100° C. for two hours. The reaction mixture was cooled in an ice-bath and the solid separated was filtered off. The filtrate was evaporated to dryness. The residue was dissolved in a methanol-chloroform mixture and concentrated to a syrup. The purification of the residue by flash vacuum chromatography over a silica gel column eluting sequentially with chloroform-methanol (70:1), chloroform-methanol (50:1) and finally chloroform-methanol (30:1), yielding 23 g (70%) of 3'-azido-2',3'-dideoxyuridine.

Provenance & Evidence