Adenine → HCID 474172, compound

Participants

Reaction Conditions

Reaction Steps

1,4-Anhydro-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-D-ribitol was prepared from 5-benzoyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose by conversion to 5-O-benzoyl-3-deoxy-1-methoxy-α(β)-D-ribofuranose with methanolic HC1, demethoxylation of the latter followed by tosylation of the 2-position with tosyl chloride and pyridine. A mixture of adenine (0.354 g, 2.62 mmol), potassium carbonate (0.362 g, 2.62 mmol), 18-crown-6(0.347 g, 1.31 mmol), and 1,4-anhydro-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-D-ribitol in DMF (11 mL) was stirred at 75° C. for 11 h. The solvent was removed under reduced pressure. The residue was purified by flash chromatography with 5% MeOH/CHC113 and afforded 0.269 g (0.793 mmol, 60.5%) of the 5'-benzoate of the title compound as a white solid: mp 193°-195° C.; 1H NMR (CDC13): δ2.13-2.22 (m,1H),2.74-2.84 (m,1H),4.12(dd,1H),4.29(dd,1H),4.39-4.50(m,2H),4.59(dd,1H),5.32(m,1H),6.00(s,2H),7.40(t,2H),7.53(t ,1H),7.98(d,1H),8.02(s 1H),8.31(s,1H); UV(MeOH) λmax 260 nm.

Provenance & Evidence