On the Hydrogenation of Glycosyl Oxazolines

An investigation is undertaken into the propensity of glycosyl oxazolines to undergo reductive cleavage by catalytic hydrogenation. Results indicate that the protecting groups on carbohydrate hydroxyl groups modulate the rate of glycosyl oxazoline reduction; electron-withdrawing ester groups curtail reaction so that reductive cleavage of benzyl ethers and esters, or reduction of azide elsewhere in the molecule may be readily achieved.