Triphenylphosphine → 5'-Carbethoxymethylene-3'-amino-5',3'-dideoxythymidine

Participants

Reaction Steps

Triphenylphosphine (786 mg; 3 mM) was added to a stirred solution of the ester of Example 7 (16; 700 mg: 2.09 mM) in THF/H2O (10 ml/l ml) and the reaction was monitored by gas evolution via an attached gas bubbler. The reaction was completed after 3 hours. The mixture was evaporated in vacuo and the crude oil was chromatographed over SiO2 (50 g), eluting with 5% saturated. ammonia in methanol/ethyl acetate to afford a 93% yield (600 mg) of the title compound. Rf =0.3 (5% saturated. NH3 /MeOH in EtOAc). FAB-MS: MH+=310.

Provenance & Evidence