20705-59-3

Usage

Uses

Used in Organic Synthesis:
4-Tetrahydropyranyloxy-butan-2-one 90% is used as a protecting group in organic synthesis for the carbonyl group of butan-2-one. The THP group can be selectively removed under mild acidic conditions, allowing for the controlled synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Tetrahydropyranyloxy-butan-2-one 90% is used as an intermediate in the synthesis of various drug molecules. The THP protecting group allows for the selective protection and deprotection of the carbonyl group, enabling the synthesis of complex drug candidates with multiple functional groups.
Used in Flavor and Fragrance Industry:
4-Tetrahydropyranyloxy-butan-2-one 90% is also used in the flavor and fragrance industry as a building block for the synthesis of various aroma chemicals. The THP protecting group allows for the selective modification of the butan-2-one core, enabling the creation of novel fragrance compounds with unique scent profiles.
Used in Material Science:
In material science, 4-Tetrahydropyranyloxy-butan-2-one 90% can be used as a precursor for the synthesis of novel polymers and materials with specific properties. The THP protecting group allows for the controlled synthesis of polymers with tailored chemical and physical properties, such as solubility, stability, and reactivity.

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 590-90-9 1-Hydroxy-3-butanone 
• 142-68-7 TETRAHYDROPYRANE 
• 40365-61-5 2-(but-3-yn-1-yloxy)tetrahydropyran 
• 97250-23-2 2-[2-(2-Methyl-[1,3]dioxolan-2-yl)-ethoxy]-tetrahydro-pyran 

Downstream Products

• 162377-97-1 5-(cyclopropylidene)pentan-1-ol 
• 78501-53-8 4-O-(5'-phenacyloxycarbonylpentanoyl)-15-O-<5'-O-(tetrahydro-2''-pyranyl)mevalonyl>verrucarol 

Relevant academic research and scientific papers

Application of chiral 2-isoxazoline for the synthesis of syn-1,3-diol analogs

The asymmetric cycloaddition of TIPS nitronate catalyzed by “Cu(II)-bisoxazoline” gave the 2-isoxazoline product in 95% yield, which was converted into tert-butyl (3S,5R)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate in 14 steps through a β-hydroxy ketone.

A Method for the Late-Stage Formation of Ketones, Acyloins, and Aldols from Alkenylstannanes: Application to the Total Synthesis of Paecilonic Acid A

Treatment of alkenylstannanes with Cu(OAc)2/Et3N affords the corresponding enol esters or ketones under conditions that proved compatible with many common functionalities; these include groups that would neither survive under the sta

Synthesis of triphenylphosphonium Vitamin E derivatives as mitochondria-targeted antioxidants

A series of mitochondria-targeted antioxidants comprising a lipophilic triphenylphosphonium cation attached to the antioxidant chroman moiety of vitamin E by an alkyl linker have been prepared. The synthesis of a series of mitochondria-targeted vitamin E derivatives with a range of alkyl linkers gave compounds of different hydrophobicities. This work will enable the dependence of antioxidant defence on hydrophobicity to be determined in vivo.

Synthesis of natural maleimides farinomaleins C-E and evaluation of their antifungal activity

A practical and convenient synthesis of naturally occurring farinomaleins C-E was achieved starting from readily available ethyl 3-methyl-2-oxobutyrate and triethyl phosphonoacetate. The key steps of the sequence included a Horner-Wadsworth-Emmons condensation to obtain the precursor farinomalein A and coupling with suitable alcohols to install the chain. The synthesis of farinomalein D has been achieved starting from (R)-isopropylideneglycerol on the basis of which the S configuration was assigned to the natural compound. The antifungal activity of the synthesized compounds was evaluated against Cladosporium cladosporioides.

Synthesis of natural maleimides farinomaleins C-E and evaluation of their antifungal activity

A practical and convenient synthesis of naturally occurring farinomaleins C-E was achieved starting from readily available ethyl 3-methyl-2-oxobutyrate and triethyl phosphonoacetate. The key steps of the sequence included a Horner-Wadsworth-Emmons condensation to obtain the precursor farinomalein A and coupling with suitable alcohols to install the chain. The synthesis of farinomalein D has been achieved starting from (R)-isopropylideneglycerol on the basis of which the S configuration was assigned to the natural compound. The antifungal activity of the synthesized compounds was evaluated against Cladosporium cladosporioides.

Probing a biomimetic approach to mycaperoxide B: Hydroperoxidation studies

Hydroperoxidation studies on a series of alkene substrates demonstrate the introduction of the hydroperoxide functional group into the required position for a biosynthetically inspired synthesis of mycaperoxide B. Georg Thieme Verlag Stuttgart.

Stereospecific palladium(0)-catalyzed reduction of 2-cyclobutylidenepropyl esters. A versatile preparation of diastereomeric monoterpenoids: (±)-fragranol and (±)-grandisol

Mixtures of (E and Z)-2-cyclobutylidenepropyl sulfonates, readily available from α,α-disubstituted cyclobutanones arising from suitable cyclopropane derivatives ring expansion, underwent regioselective and stereospecific reduction by formate anion to offer, through π-1,1- trimethyleneallylpalladium complexes formed upon treatment with palladium(0), a new and convenient entry to the diastereomeric four-membered ring monoterpenoids (±)-fragranol and (±)-grandisol.

Deprotection of acetals and silyl ethers using a polymer-supported π- acid catalyst: Chemoselectivity and polymer effect

A polymeric dicyanoketene acetal (DCKA), prepared from a styrene monomer bearing dicyanoketene acetal functionality, was found to be an effective and recyclable catalyst in the chemoselective deprotection of acetals and silyl ethers. A remarkable acceleration accountable for the polymer effect was observed.

Chemistry of aldolate dianions. Effects of β-heteroatom substituents on ketone enolization

β-Hydroxy ketones can be doubly deprotonated with >2 equiv of an amide base at low temperature providing both proximal or distal aldolate dianions in good to excellent yield. A variety of substitutionally biased β-hydroxy ketones give exclusively distal dianions. If the distal site is blocked, proximal dianions are formed in good yield; however, Chromatographic separation of the silylated products leads to decreased yields. Comparative enolization studies of 4-hydroxy-2-butanone, l-hydroxy-3-pentanone, and hydroxyl-substituted derivatives reveal a kinetic factor favoring proximal deprotonation of β-OTMS and β-alkoxy ketones. However, there is a thermodynamic factor favoring distal dianions that becomes significant as solutions of the dianions are warmed. Thermal stability studies indicate good room temperature stability of the dianions toward elimination and retroaldolization processes; control studies in this area also support the presence of a dianionic species. Precedent suggests that the dianions exist as internally chelated species, and we speculate that ion triplets containing bridging lithiums are good candidates for the structure of both proximal and distal dianion species. The distal dianions undergo clean reaction with aldehydes and acyl cyanides leading to β,β′-dihydroxy ketones and β-hydroxy-β′-oxo ketones, respectively.

Pd(II)-CATALYZED ACETAL/KETAL HYDROLYSIS/EXCHANGE REACTIONS

PdCl2(CH3CN)2 catalyzes the hydrolysis of dioxolane acetals and ketals in moist CH3CN, while in acetone, efficient and more reproducible exchange reactions take place.