反应详情

5'-O-Acetyl-3'-azido-3'-deoxythymidine was reacted with 5 equivalents of 1,2,4-triazole and two equivalents of 4-chlorophenyl dichlorophosphate in dry pyridine at ambient temperature for 10 days. Silica gel chromatography of the crude product using 1:1 EtOAc/hexane (v/v) followed by combination and evaporation of the appropriate fractions yielded an oil. Crystallization from EtOAc afforded the title compound as a solid 2.7 g (7.5 mMol; 60%); m.p.=143°-145° C. UV (nm): at pH 1λmax =324,245,215 (ε=9300, 10000, 20500), λmin =282,233 (ε=2100,8200); at pH 13λmax =276 (ε=6000), λmin =242 (ε=2000), H1NMR (DMSO-d6) δ9.34, 8.40(2s,2H, triazolyl), δ8.23(s,1H,H6), δ6.12(t, 1H, H1', J=6.16 Hz), β4.48-4.17(m, 4H, H3', H4', H5'), δ2.35(s, 3H, 5'-acetyl), δ2.07(s, 3H, 5CH3).

1. customfollowed by combination and evaporation of the appropriate fractions
2. customyielded an oil
3. customCrystallization from EtOAc