Phenyloxazoline derivatives of amino-sugars. Part II. The fission of phenyloxazolines under basic conditions

Abstract

Benzyl 2,3-dideoxy-5,6-O-isopropylidene-2′-phenyl-β-D-allofuranosido[2,3-d]-Δ^2′-oxazoline (6) was hydrolysed to the corresponding benzamido-alcohol (10) on treatment with toluene-p-sulphonic acid in aqueous pyridine at 100°, conditions which did not hydrolyse the O-isopropylidene group. Compound (6) was degraded by potassium t-butoxide in dimethyl sulphoxide at 80° to a mixture of products including the enamide (12) and the benzamido-alcohol (10).