Tetrahydropyran

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.^[1][2] 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.^[3]

• Tetrahydrofuran (THF)
• Pyran

1. ^ Organic Syntheses, Coll. Vol. 7, p.334 (1990); Vol. 60, p.81 (1981) Article.
2. ^ Organic Syntheses, Coll. Vol. 7, p.160 (1990); Vol. 64, p.80 (1986) Article.
3. ^ Organic Syntheses, Coll. Vol. 3, p.794 (1955); Vol. 23, p.90 (1943).Article

nl:Tetrahydropyraan Template:WH Template:WS