Trifluoroacetic acid → HCID 18394988, compound

Participants

Reaction Steps

The product of Example 1 step (i), (5-(hydroxy-(1,1-diphenyl)methyl)-2',3',5'-tris-O-((1,1-dimethylethyl)dimethylsilyl)uridine) (6.8 g), was dissolved in dichloromethane (80 ml) and triethylsilane (1.83 ml) and treated with trifluoroacetic acid (1.38 ml). After stirring for 20 minutes the solvents were removed under reduced pressure and any remaining traces removed by azeotroping three times with toluene. The remaining residue was dissolved in dimethylformamide (5 ml) and treated with imidazole (0.54 g) and t-butyldimethylsilylchloride (0.6 g). After stirring for 16 hours the mixture was partitioned between water and iso-hexane and the organic phase was washed with water, collected and dried over magnesium sulphate. The solvent was removed under reduced pressure and the residue was purified by flash silica-gel chromatography eluting with ethyl acetate/iso-hexane mixtures to afford 5-diphenylmethyl-2',3',5'-tris-O-((1,1-dimethylethyl)dimethylsilyl)uridine as a colourless foam (5.94 g).

Provenance & Evidence