Water → HCID 69637519, compound

Participants

Reaction Steps

Triphenylphosphine (600 mg, 2.4 mmol) was added to a stirred solution of (R)-5-(2-azido-(S)-1-hydroxyethyl)-3,4-dibenzyloxy-5H-furan-2-one (5) (750 mg, 2 mmol) in THF (10 ml) and after a few minutes gas was evolved. The stirring was continued until the effervescence had ceased (typically 2-3 h) and water (2 ml) was then added and the mixture stirred for a further 1 hour. The THF was removed under reduced pressure and the residue partitioned between dichloromethane (25 ml) and water (25 ml). The organic phase was separated, dried (MgSO4), filtered and any volatile components evaporated under reduced pressure (45° C. at 8 mm/Hg) to leave a viscous orange residue which was purified by chromatography on silica. Initial elution with a dichloromethane:methanol (19:1) mixture removed the less polar by-products and the product was then isolated by elution with a dichloromethane:methanol (3:1) mixture as a pale yellow oil (150 mg; 21%) (Rf0.25).

Provenance & Evidence