What is Tetrahydropyran?

Description

Tetrahydropyran (THP) is an organic compound with the chemical formula C5H10O. This compound is a cyclic ether that occurs in various biologically active compounds ranging from marine toxins, through pheromones to cytostatics and pharmaceutical agents. Because THP moieties are widely found in biologically active compounds and their intermediates, they stand out as attractive targets for synthetic organic chemistry[1]. Tetrahydropyran is useful synthons for biologically important compounds.

Synthesis

Nowadays, numerous synthetic routes provide THPs, including hydrogenation of dihydropyran using a platinum black catalyst; heating pentamethylene bromide with water; or with water and zinc oxide in a sealed tube; or heating pentamethylene glycol with 3 volumes of 60% sulfuric acid in a pressure tube, or dehydration of this glycol in the vapor phase over kaolin or aluminum oxide[1].

Uses

Tetrahydropyrans and furans principally constitute a central motif in diverse medicinally privileged molecules. The most notable anticancer agents, bryostatin, and eribulin are marine macrolides having intriguing tetrahydropyran and furan motifs There is a large number of marine macrolide natural products that contain tetrahydropyran and tetrahydrofuran ring together. For instance, goniodomin A(actin targeting polyether), prorocentrolide (toxin halistatins), and percent toxins. This compound and its derivatives were effective as NK1 receptor antagonists and used in treating depression and mood disorders[2]. Its derivative, THP ether, is more common. THP ether is prepared by the reaction of alcohols and 3,4-dihydropyran. In particular, the 2-tetrahydropyran (THP) group is a common protecting group for alcohol.

References

[1] Kurbanova A, et al. Preparation of functionalised tetrahydropyrans catalysed by isoreticular zeolites. Microporous and Mesoporous Materials, 2023; 350: 112463.

[2] Yadav R, et al. One-pot strategy: A highly economical tool in organic synthesis and medicinal chemistry. Green Approaches in Medicinal Chemistry for Sustainable Drug Design, 2020; 353-425.