1. Hydrogenolytic cleavage of naphthylmethyl ethers in the presence of sulfides
- Author
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Philip O. Adero, Dean R. Jarois, and David Crich
- Subjects
010405 organic chemistry ,organic chemicals ,Organic Chemistry ,General Medicine ,Naphthalenes ,Sulfides ,010402 general chemistry ,Cleavage (embryo) ,01 natural sciences ,Biochemistry ,Article ,0104 chemical sciences ,Analytical Chemistry ,chemistry.chemical_compound ,Thioether ,chemistry ,Hydrogenolysis ,Organic chemistry ,Ethers ,Hydrogen - 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.
- Published
- 2017
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