Hydrogenolytic cleavage of naphthylmethyl ethers in the presence of sulfides

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Abstract

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.

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Adero, P. O., Jarois, D. R., & Crich, D. (2017). Hydrogenolytic cleavage of naphthylmethyl ethers in the presence of sulfides. Carbohydrate Research, 449, 11–16. https://doi.org/10.1016/j.carres.2017.06.011

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