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* [[Tetrahydrofuran]] (THF)
* [[Tetrahydrofuran]] (THF)
* [[Pyran]]
* [[Pyran]]

== Alcohol Protection ==
In organic synthesis, 2-tetrahydropyranyl group ('''THP''') is used as a [[protecting group]] for [[alcohols]].
[[File:THP_Ether.png|link=https://en.wikipedia.org/wiki/File:THP_Ether.png|thumb]]

=== Most common protection methods ===
* Treatment of alcohol with [[dihydropyran]] and ''p''-toluenesulfonic acid in [[dichloromethane]] at ambient temperature<ref name=":0">{{Cite book|url=http://doi.wiley.com/10.1002/0470053488|title=Greene's Protective Groups in Organic Synthesis, Fourth Edition - Wuts - Wiley Online Library|last=Wuts|first=Peter G. M.|last2=Greene|first2=Theodora W.|doi=10.1002/0470053488}}</ref>
[[File:THPProtection.png|link=https://en.wikipedia.org/wiki/File:THPProtection.png|none|thumb|610x610px]]
<ref>{{Cite journal|last=Robinson|first=Anna|last2=Aggarwal|first2=Varinder K.|date=2010-09-03|title=Asymmetric Total Synthesis of Solandelactone E: Stereocontrolled Synthesis of the 2-ene-1,4-diol Core through a Lithiation–Borylation–Allylation Sequence|url=http://onlinelibrary.wiley.com/doi/10.1002/anie.201003236/abstract|journal=Angewandte Chemie International Edition|language=en|volume=49|issue=37|pages=6673–6675|doi=10.1002/anie.201003236|issn=1521-3773}}</ref>
* 2-hydroxytetrahydropyranyl, [[triphenylphosphine]], [[diethyl azodicarboxylate]] (DEAD) in THF

=== Most common deprotection methods ===
* [[Acetic acid]] (AcOH) in THF/water solution or ''[[P-Toluenesulfonic acid|p]]''[[P-Toluenesulfonic acid|-toluenesulfonic acid]] in water
* [[Pyridinium p-toluenesulfonate|Pyridinium ''p''-toluenesulfonate]] (PPTS) in [[ethanol]]


==References==
==References==

Revision as of 03:20, 10 June 2016

Tetrahydropyran
Tetrahydropyran
Tetrahydropyran
THP
THP
Names
IUPAC name
Oxane
Other names
Tetrahydropyran,
Oxacyclohexane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.005.048 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C5H10O/c1-2-4-6-5-3-1/h1-5H2 checkY
    Key: DHXVGJBLRPWPCS-UHFFFAOYSA-N checkY
  • InChI=1/C5H10O/c1-2-4-6-5-3-1/h1-5H2
    Key: DHXVGJBLRPWPCS-UHFFFAOYAV
  • O1CCCCC1
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).
checkY verify (what is checkY☒N ?)

Tetrahydropyran (THP) is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. 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.[1]

Preparation

One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation with Raney nickel of dihydropyran.[2]

Reactions

In organic synthesis, the 2-tetrahydropyranyl group is used as a protecting group for alcohols.[3][4] 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

See also

Alcohol Protection

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

Most common protection methods

[6]

Most common deprotection methods

References

  1. ^ 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.
  2. ^ D. W. Andrus; John R. Johnson (1955). "Tetrahydropyran". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 3, p. 794.
  3. ^ R. A. Earl L. B. Townsend (1990). "Methyl 4-Hydroxy-2-butynoate". Organic Syntheses; Collected Volumes, vol. 7, p. 334.
  4. ^ Arthur F. Kluge (1990). "Diethyl [(2-Tetrahydropyranyloxy)methyl]phosphonate". Organic Syntheses; Collected Volumes, vol. 7, p. 160.
  5. ^ Wuts, Peter G. M.; Greene, Theodora W. Greene's Protective Groups in Organic Synthesis, Fourth Edition - Wuts - Wiley Online Library. doi:10.1002/0470053488.
  6. ^ 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.
source: https://en.wikipedia.org/w/index.php?title=Tetrahydropyran&diff=prev&oldid=724570404

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