Is tetrahydropyran an ether?
Tetrahydropyran (THP) is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. 2-Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and 3,4-dihydropyran are commonly used as protecting groups in organic synthesis.
Which solvent favors deprotection of THP ether?
THP ethers are formed under acidic conditions from alcohols and dihydropyran. The deprotection is usually performed as an acidic hydrolysis or alcoholysis. Some new methods also allow the protection and deprotection of acid-sensitive molecules by using mild Lewis acids.
How is Tetrahydropyran formed?
The reaction of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room temperature gives tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Various fragrant compounds have been synthesized using this method.
What is pyran ring?
In chemistry, pyran, or oxine, is a six-membered heterocyclic, non-aromatic ring, consisting of five carbon atoms and one oxygen atom and containing two double bonds. The term pyran is also often applied to the saturated ring analog, which is more properly referred to as tetrahydropyran (oxane).
Is Tetrahydropyran polar?
Information on this page: Normal alkane RI, non-polar column, custom temperature program. References. Notes.
What is a cyclic ether?
Cyclic ethers are the class of heterocyclic monomers that provide suitable models for mechanistic studies. On the other hand, polymerization of several monomers of this class leads to polymeric materials that are produced on an industrial scale. The most prominent examples are polymers of EO, PO, ECH, or THF.
Is tetrahydropyran polar?
How do you make THF?
DuPont developed a process for producing THF by oxidizing n-butane to crude maleic anhydride, followed by catalytic hydrogenation. A third major industrial route entails hydroformylation of allyl alcohol followed by hydrogenation to 1,4-butanediol.
Why are acetals good protecting groups?
The importance of acetals as carbonyl derivatives lies chiefly in their stability and lack of reactivity in neutral to strongly basic environments. This cannot be done without a protecting group because Grignard reagents react with esters and ketones. …
What is a tetrahydropyranyl ether?
Although tetrahydropyran is an obscure compound, tetrahydropyranyl ethers are commonly used in organic synthesis. Specifically, the 2-tetrahydropyranyl (THP) group is a common protecting group for alcohols. Alcohols react with 3,4-dihydropyran to give 2-tetrahydropyranyl ethers.
What is the IUPAC name of the compound tetrahydropyranyl?
In 2013, its preferred IUPAC name was established as oxane. The compound is a colourless volatile liquid. Derivatives of tetrahydropyran are, however, more common. 2-Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and 3,4-dihydropyran are commonly used as protecting groups in organic synthesis.
How is the tetrahydropyranyl ether of cholesterol deprotected?
Under the same conditions, the tetrahydropyranyl ether of cholesterol was also efficiently deprotected. A mechanism was proposed which involved an initial hydrogen abstraction, followed by quenching of the resulting stabilized cation by water (Scheme 6 ).
How to protect hydroxyl groups as tetrahydropyranyl ethers?
A simple and convenient synthetic protocol for the protection of hydroxyl groups as tetrahydropyranyl ethers as well as carbonyl functionalities as oxathioacetals and thioacetals has been achieved using a catalytic amount of silica-supported perchloric acid under solvent-free conditions.