HCID 11059478, compound → HCID 10966793, compound

Participants

Reaction Steps

A solution of 1-(3,5-di-O-benzoyl-2-deoxy-β-L-xylofuranosyl)-5-fluorouracil (6b) (0.25 g, 0.55 mmol) in ammoniacal methanol (25 ml) is stirred overnight at room temperature. The solution is evaporated under reduced pressure and the residue is evaporated several times with methanol. The crude material obtained is dissolved in water and the resulting solution is washed several times with chloroform. The aqueous phase is evaporated and the residue is directly crystallized from methanol to give 115 mg (yield 85%) of pure 7b: m.p.=198-200° C.; UV [EtOH 95] λmax 267 nm (ε, 8500), λmin 233 nm (ε, 2100); 1H NMR (DMSO-d6) δ ppm=11.79 (s, 1H, 3-NH), 8.16 (d, 1H, H-6; J=7.4 Hz), 6.05 (dd, 1H, H-1′; J=1.8 and 6.5 Hz), 5.38 (d, 1H, OH-3′; J=3.3 Hz), 4.73 (t, 1H, OH-5′; J=5.4 Hz), 4.30-4.20 (m, 1H, H-3′), 3.85-3.60 (m, 3H, H-4′,5′ and 5″), 2.60-2.50 (m, 1H, H-2′ partially obscured by DMSO-d5), 1.90 (dd, 1H H-2″; J=1.8 and 14.7 Hz); mass spectra (matrix: glycerol-thioglycerol, 50:50, v/v): FAB>0 339 [M+glycerol+H]+, 247 [M+H]+, 131 [BH2]+ and 115 [s]+; FAB<0 245 [M−H]− and 129 [B]−.

Provenance & Evidence