Hydroxyamine hydrochloride → Thymine

Participants

Reaction Conditions

Reaction Steps

A solution of the 4'-α and 4'-β isomers 3'-O-t-butyldimethylsilyl-4'-formylthymidine (380 mg, 1 mM), the compound of Formula 12, prepared, e.g., as described in Preparation 8, with H2NOH HCl (110 mg, 1.6 mM) in pyridine (1.5 ml) was stirred at 24° C. for 16 hours. The solvent was removed by evaporation. The residue was partitioned between H2O (5 ml) and EtOAc (15 ml). The aqueous layer was extracted with EtOAc (10 ml), and the EtOAc fractions were combined. The solvent was removed by evaporation and the residue was purified on a thick silica gel plate (60% EtOAc/hexane), 3'-O-t-butyldimethylsilyl-4'-hydroxyiminomethylthymidine (148 mg, 0.37 mM). MS (399 M+).

Provenance & Evidence