Carbon-13 NMR spectra of saturated heterocycles. XI. Tetrahydropyrans (oxanes) was written by Eliel, Ernest L.;Manoharan, Muthiah;Pietrusiewicz, K. Michal;Hargrave, Karl D.. And the article was included in Organic Magnetic Resonance in 1983.Reference of 13417-49-7 This article mentions the following:
The 13C NMR spectra of 62 oxanes (tetrahydropyrans) with and without Me substituents at various ring positions, some of them bearing in addition (or instead) Et, vinyl, ethynyl, carbomethoxy, and methylol substituents at C-2, have been recorded, and the 294 resulting chem. shifts have been correlated by multiple linear regression anal. Axial and equatorial α-, β-, γ-, δ-, gem– and vic-parameters for shifts caused by Me groups at all ring positions, and similar parameters for the other substituents at C-2, are reported. Standard deviations of the parameters are, in most cases, within 0.3 ppm and the agreement of calculated and exptl. shifts is excellent. 13C NMR spectra of a number of addnl. substituted tetrahydropyrans, and of 3,6-dihydro-2H-pyrans and 3,4-dihydro-2H-pyrans, are tabulated and discussed. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7Reference of 13417-49-7).
5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Numerous natural products have tetrahydropyran skeleton as the building block for designing new natural products and their derivatives e.g. aplysiatoxins, avermectins, oscillatoxins, talaromycins, latrunculins and acutiphycins. One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation of the 3,4-isomer of dihydropyran with Raney nickel.Reference of 13417-49-7
Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics