Selective removal of the (2-naphthyl)methyl protecting group in the presence of p-methoxybenzyl group by catalytic hydrogenation

Selective cleavage of the (2-naphthyl)methyl (NAP) group in the presence of p-methoxybenzyl (PMB), benzyl and benzylidene groups was achieved by catalytic hydrogenation with a series of monosaccharides. At a disaccharide level, the PMB group was stable upon hydrogenolysis of the NAP, however, partial cleavage of benzyl ether functions was observed.