Tetrahydropyran

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Tetrahydropyran
Tetrahydropyran
THP
Names
IUPAC name
Oxane
Other names
Tetrahydropyran,
Oxacyclohexane
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.005.048
KEGG
UNII
Properties
C5H10O
Molar mass 86.13 g/mol
Density 0.880 g/cm3
Melting point −45 °C (−49 °F; 228 K)
Boiling point 88 °C (190 °F; 361 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tetrahydropyran (THP) is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. It is named by reference to pyran, which contains two double bonds, and may be produced from it by adding four hydrogens to that compound. In 2013, its preferred IUPAC name was established as oxane.[1] The compound is a colourless volatile liquid, but is obscure. Derivatives of tetrahydropyran are, however, more common. Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and dihydropyran are common intermediates in organic synthesis. Furthermore, a tetrahydropyran ring system, i.e., five carbon atoms and an oxygen, is the core of pyranose sugars, such as glucose. In gas phase, the THP exists in its lowest energy Cs symmetry chair conformation.[2]

Preparation[edit]

One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation with Raney nickel of dihydropyran.[3]

Reactions[edit]

In organic synthesis, the 2-tetrahydropyranyl group is used as a protecting group for alcohols.[4][5] 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.

THP protective groups

Alcohol protection[edit]

In organic synthesis, 2-tetrahydropyranyl group (THP) is used as a protecting group for alcohols.

THP Ether.png

Most common protection methods[edit]

THPProtection.png

[7]

Most common deprotection methods[edit]

See also[edit]

References[edit]

  1. ^ "New IUPAC Organic Nomenclature - Chemical Information BULLETIN" (PDF). 
  2. ^ Builth-Williams, J. D.; Bellm, S. M.; Chiari, L.; Thorn, P. A.; Jones, D. B.; Chaluvadi, H.; Madison, D. H.; Ning, C. G.; Lohmann, B. (2013-07-21). "A dynamical (e,2e) investigation of the structurally related cyclic ethers tetrahydrofuran, tetrahydropyran, and 1,4-dioxane". The Journal of Chemical Physics. 139 (3): 034306. doi:10.1063/1.4813237. ISSN 0021-9606. 
  3. ^ D. W. Andrus; John R. Johnson (1955). "Tetrahydropyran". Org. Synth. ; Coll. Vol., 3, p. 794 
  4. ^ R. A. Earl L. B. Townsend (1990). "Methyl 4-Hydroxy-2-butynoate". Org. Synth. ; Coll. Vol., 7, p. 334 
  5. ^ Arthur F. Kluge (1990). "Diethyl [(2-Tetrahydropyranyloxy)methyl]phosphonate". Org. Synth. ; Coll. Vol., 7, p. 160 
  6. ^ Wuts, Peter G. M.; Greene, Theodora W. Greene's Protective Groups in Organic Synthesis, Fourth Edition - Wuts - Wiley Online Library. doi:10.1002/0470053488. 
  7. ^ Robinson, Anna; Aggarwal, Varinder K. (2010-09-03). "Asymmetric Total Synthesis of Solandelactone E: Stereocontrolled Synthesis of the 2-ene-1,4-diol Core through a Lithiation–Borylation–Allylation Sequence". Angewandte Chemie International Edition. 49 (37): 6673–6675. doi:10.1002/anie.201003236. ISSN 1521-3773.