Abstract: Disclosed are cis-2,6-disubstituted tetrahydropyran derivatives represented by Chemical Formula 1 and a preparation method thereof. The tetrahydropyran derivatives can be prepared by Prins-reacting tetrahydropyran derivatives with homopargylicalcohol derivatives in the presence of trimethylsilyltriflate. The tetrahydropyran derivatives with cis-substituents at both C2 and C6 positions of the tetrahydropyran ring are useful as intermediates for use in the synthesis and development of therapeutically effective, naturally occurring compounds. (wherein, R1, R2 and R3 are as defined in the specification.).