Thymine → HCID 511979, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of thymine (0.142 g, 1.12 mmol), potassium carbonate (0.208) g, 1.5 mmol), 18-crown-6(0.119 g, 0.45 mmol) and 1,4-anhydro-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-D-ribitol (0.283 g, 0.75 mmol) in DMF (5 mL) was stirred at 75° C. for 14 h. The solvent was removed under reduced pressure. The residue was purified by flash chromatography using 5% methanol/chloroform as the mobile phase to afford 0.074 g (0.224 mmol, 30%) of the protected isothymidine. To a solution of this nucleoside (0.074 g, 0.22 mmol) in methanol (3.5 mL), was added sodium methoxide (0.018 g, 0.33 mmol). After stirring for 2 h at room temperature, the reaction mixture was neutralized with 5N acetic acid (2 drops). The solvent was removed under reduced pressure and the residue was purified on a silica gel plate with 10% methanol/chloroform to afford the title compound (0.18 mmol, 82%) as a very hygroscopic white solid: 1H NMR (Me2SO-d6): δ1.76 (m,4H),2.35(m,1H),3.45-3.52(m,1H),3.65(m,1H),3.72-3.87(m,3H),4.95(t,1H),5.1(m,1H),7.61(s,1H),11.21(s,1H; UV(MeOH)λmax 271 nm(ε9,554); [α]D =(+)26° (c=0.2,MeOH): FTIR(KBr)1670 cm-1 ; mass spectrum, m/z 226(M+).

Provenance & Evidence