Tetrahydropyran

Overview
Tetrahydropyran, or oxane, is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom.

The tetrahydropyran ring system is the core of pyranose sugars.

In organic synthesis, the 2-tetrahydropyranyl group is used as a protecting group for alcohols. Reaction of the alcohol with dihydropyran forms a tetrahydropyranyl ether, protecting the alcohol from a variety of reactions. The alcohol can later be restored readily by acidic hydrolysis with formation of 5-hydroxypentanal.



One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation with Raney nickel of dihydropyran.