[C:1]([CH:4]([OH:22])[C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[C:16](I)[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:7][C@@H:6]1[N:19]=[N+:20]=[N-:21])(=[O:3])[CH3:2].[C-]#N.[K+].CC([O-])=O.[K+].[N:31]([C@@H:34]1[C@@H](CO)O[C@@H](N2C=C(C)C(=S)NC2=O)C1)=[N+]=[N-]>CS(C)=O>[C:1]([CH:4]([OH:22])[C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[C:16]([C:34]#[N:31])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:7][C@@H:6]1[N:19]=[N+:20]=[N-:21])(=[O:3])[CH3:2]5'-Acetyl-3'-azido-2',3'-dideoxy-5-iodouridine(0.5 g, 1.2 mMol, Ex.) was treated with KCN(0.1 g, 1.6 mMol) and KOAc(0.15 g, 1.6 mMol) in anhydrous DMSO at 105° C. for 90 minutes in a method analogous to (1). The DMSO was evaporated in vacuo and the residue chromatographed on silica gel, eluted with CHCl3 then with 20:1 CHCl3/MeOH (v/v). Collection of appropriate fractions followed by evaporation of the solvents gave pure 5'-acetyl-3'-azido-5-cyano-2',3'-dideoxyuridine. This material was dissolved in NH3 saturated MeOH at ambient temperature and allowed to stand overnight. The solvents were evaporated in vacuo and the residue chromatographed on silica gel using 9:1 CHCl3/MeOH (v/v) as the eluting solvent. Collection and evaporation of the appropriate fractions yielded the title compound as a clear oil: UV(nm): at pH 1 λmax=276,214 (ε=13700,12800), λmin=238 (ε=2200); at pH 13 λmax=275 (ε=10000), λmin=245(ε=3200); H NMR(DMSO-d6) δ8.81(s,1H,H6), 5.95(dd,1H,H1',J=2.34,4.11 Hz), 5.45(t,1H,5'OH,J=5.08 Hz), 4.4-4.3(m,1H,H3'), 3.9-3.8(m,1H,H4'), 3.8-3.5(m,2H,H5'), 2.45-2.30(m,2H,H2').
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