Hydrogenolytic cleavage of naphthylmethyl ethers in the presence of sulfides

With the aid of a series of model thioether or thioglycoside containing polyols protected with combinations of benzyl ethers and 2-naphthylmethyl ethers it is demonstrated that the latter are readily cleaved selectively under hydrogenolytic conditions in the presence of the frequently catalyst-poisoning sulfides. These results suggest the possibility of employing 2-naphthylmethyl ethers in place of benzyl ethers in synthetic schemes when hydrogenolytic deprotection is anticipated in the presence of thioether type functionality. [Display omitted] •Hydrogenolytic cleavage in presence of thioglycosides.•Selective hydrogenolysis.•Deprotection of thioglycosides.