20443-91-8

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 100-02-7 4-nitro-phenol 
• 694-54-2 tetrahydro-2H-2-pyranol 

Downstream Products

• 100-02-7 4-nitro-phenol 
• 824-78-2 4-nitrophenol sodium salt 
• 97389-23-6 4-[(2-tetrahydropyranyloxy)methyl]aniline 
• 72036-48-7 C₅H₉O⁽¹⁺⁾ 
• 830-03-5 4-nitrophenol acetate 
• 174359-53-6 ((S)-2-tert-Butoxycarbonylamino-propionylamino)-acetic acid 4-benzyloxycarbonylamino-phenyl ester 
• 174359-54-7 ((R)-2-tert-Butoxycarbonylamino-propionylamino)-acetic acid 4-benzyloxycarbonylamino-phenyl ester 
• 174359-48-9 (S)-2-tert-Butoxycarbonylamino-propionic acid 4-benzyloxycarbonylamino-phenyl ester 
• 174359-49-0 (R)-2-tert-Butoxycarbonylamino-propionic acid 4-benzyloxycarbonylamino-phenyl ester 
• 1026605-29-7 ((S)-2-tert-Butoxycarbonylamino-propionylamino)-acetic acid 4-amino-phenyl ester 
• 1025987-97-6 ((R)-2-tert-Butoxycarbonylamino-propionylamino)-acetic acid 4-amino-phenyl ester 
• 174359-60-5 C₃₃H₃₇N₅O₉ 
• 174359-61-6 C₃₃H₃₇N₅O₉ 
• 174359-59-2 C₃₄H₃₈N₆O₁₀ 

Relevant academic research and scientific papers

Magnetic nanoparticle-supported DABCO tribromide: A versatile nanocatalyst for the synthesis of quinazolinones and benzimidazoles and protection/deprotection of hydroxyl groups

1,4-Diazabicyclo[2.2.2]octane tribromide supported on magnetic Fe3O4 nanoparticles (MNPs-DABCO tribromide) as a novel heterogeneous tribromide type compound was found to be an efficient and reusable nanocatalyst for the one-pot synthesis of 2-arylquinazolin-4(3H)-ones and 2-aryl-1H-benzo[d]imidazoles through oxidative cyclization of aldehydes with 2-aminobenzamides and 1,2-phenylenediamine, respectively. Also, MNPs-DABCO tribromide catalyzed trimethylsilylation/tetrahydropyranylation and desilylation/depyranylation of a wide variety of alcohols and phenols through changing the solvent medium at room temperature.

Croconamides: A new dual hydrogen bond donating motif for anion recognition and organocatalysis

We introduce bis-aryl croconamides as a new member in the family of dual hydrogen bonding anion receptors. In this study a series of croconamides are synthesised, and the selectivity for anion binding is investigated (Cl- > Br- > I- in CH2Cl2). The croconamides exhibit different structures in the crystal phase depending on the substituents on the aromatic rings, and furthermore, the crystal structure revealed the presence of tautomers. DFT calculations elucidated the complex structures formed upon addition of anion to the croconamides, confirming the order of association constants towards the halogen anions. The use of croconamides as organocatalysts in a proof-of-concept study is demonstrated in the formation of THP ethers. In addition to this, construction of a Hammet plot further elucidates the mechanism in action on formation of THP ethers.

Tetrahydropyranylation of alcohols and phenols catalyzed by a new multi-wall carbon nanotubes-bound tin(IV) porphyrin

Abstract: In the present study, tetrahydropyranylation of alcohols and phenols with 3,4-dihydro-2H-pyran (DHP) using tetrakis(p-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [SnIV(TNH2PP)(OTf)2], and tetrakis(p-aminophenyl)porphyrinatotin(IV) tetrafluoroborate, [SnIV(TNH2PP)(BF4)2], supported on multi-wall carbon nanotubes as new catalytic systems is investigated. These new catalysts, [SnIV(TNH2PP)(OTf)2@MWCNT] and [SnIV(TNH2PP)(BF4)2@MWCNT], were characterized using elemental analysis, FT-IR spectroscopic techniques, scanning electron microscopy and diffuse reflectance UV–Vis spectroscopic methods. In these catalytic systems, an optimization on the amounts of catalysts and amount of DHP was done in the tetrahydropyranylation of alcohols and phenols with DHP and the best outcomes were received in the presence of 0.01?mmol (40?mg) of [SnIV(TNH2PP)(OTf)2@MWCNT] and [SnIV(TNH2PP)(BF4)2@MWCNT] with 2?mmol of DHP. Efficiency and reusability are two important features of these new heterogenized catalysts for tetrahydropyranylation of primary, secondary and tertiary alcohols as well as phenols at room temperature. These catalysts were recovered several times with no loss on their initial activity, which indicates their high reusability and stability. Graphical Abstract: In the present study, tetrahydropyranylation of alcohols and phenols with 3,4-dihydro-2H-pyran (DHP) using tetrakis(p-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [SnIV(TNH2PP)(OTf)2], and tetrakis(p-aminophenyl)porphyrinatotin(IV) tetrafluoroborate, [SnIV(TNH2PP)(BF4)2], supported on multi-wall carbon nanotubes as new catalytic systems is investigated. These new catalysts, [SnIV(TNH2PP)(OTf)2@MWCNT] and [SnIV(TNH2PP)(BF4)2@MWCNT], were characterized using elemental analysis, FT-IR spectroscopic techniques, scanning electron microscopy and diffuse reflectance UV–Vis spectroscopic methods. In these catalytic systems, an optimization on the amounts of catalysts and amount of DHP was done in the tetrahydropyranylation of alcohols and phenols with DHP and the best outcomes were received in the presence of 0.01?mmol (40?mg) of [SnIV(TNH2PP)(OTf)2@MWCNT] and [SnIV(TNH2PP)(BF4)2@MWCNT] with 2?mmol of DHP. Efficiency and reusability are two important features of these new heterogenized catalysts for tetrahydropyranylation of primary, secondary and tertiary alcohols as well as phenols at room temperature. These catalysts were recovered several times with no loss on their initial activity, which indicates their high reusability and stability. [Figure not available: see fulltext.].

Thiosemicarbazone organocatalysis: Tetrahydropyranylation and 2-deoxygalactosylation reactions and kinetics-based mechanistic investigation

The first use of thiosemicarbazone-based organocatalysis was demonstrated on both tetrahydropyranylation and 2-deoxygalactosylation reactions. The organocatalysts were optimised using kinetics-based selection. The best catalyst outperformed previously reported thiourea catalysts for tetrahydropyranylation by 50-fold. Hammett investigations of both the organocatalyst and the substrate indicate an oxyanion hole-like reaction mechanism.

Selective tetrahydropyranylation of alcohols and phenols using titanium(IV) salophen trifluoromethanesulfonate as an efficient catalyst

Titanium(IV) salophen trifluoromethanesulfonate, [TiIV(salophen)(OSO2CF3)2], as a catalyst enables selective tetrahydropyranylation of alcohols and phenols with 3,4-dihydro-2H-pyran. Using this catalytic system, primary, secondary and tertiary alcohols, as well as phenols, were converted to their corresponding tetrahydropyranyl ethers in high yields and short reaction times at room temperature. Investigation of the chemoselectivity of this method showed discrimination between the activity of primary alcohols in the presence of secondary and tertiary alcohols and phenols. This heterogenized catalyst could be reused several times without loss of its catalytic activity. Copyright

Highly efficient protection of alcohols and phenols catalysed by tin porphyrin supported on MIL-101

The catalytic activity of 5,10,15,20-tetrakis(4-aminophenyl)porphyrinatotin(IV) trifluoromethanesulfonate, [SnIV(TNH2PP)(OTf)2], supported on chloromethylated MIL-101, was investigated in the trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) and also their tetrahydropyranylation with 3,4-dihydro-2H-pyran. Excellent yields, mild reaction conditions, short reaction times and reusability of the catalyst without significant decrease in its initial activity are noteworthy advantages of this supported catalyst.

3,5-Dinitrobenzoic acid catalyzed synthesis of 2,3-unsaturated O- and S-glycosides and tetrahydropyranylation of alcohols and phenols

A simple procedure for the synthesis of 2,3-unsaturated glycosides in acetonitrile and tetrahydropyranylation of alcohols and phenols in dichloromethane in the presence of 3,5-dinitrobenzoic acid is described. A variety of alcohols and thiols are reacted with glycals to give the desired products in high yields with high α-selectivity.

Short communication: Catalytic tetrahydropyranylation of phenols and alcohols using vanadium(V)-substituted polyoxomolybdates

Alcohols and phenols were tetrahydropyranylated in the presence of H 7[PMo8V4O40] in good to excellent yields in acetonitrile and under solventfree reaction conditions. A mild and convenient method for the formation and deprotection of ethers (THP ethers) is described. The formation of THP ethers from the corresponding alcohols was accomplished in the presence of acid-sensitive functional groups.

Tetrahydropyranylation of alcohols and phenols catalyzed by a new polystyrene-bound tin(IV) porphyrin

In the present work, tetrahydropyranylation of alcohols and phenols with 3,4-dihydro-2H-pyran (DHP) catalyzed by tetrakis(p-aminophenyl) porphyrinatotin(IV) trifluoromethanesulfonate, [SnIV(TNH 2PP)(OTf)2], supported on chloromethylated polystyrene is reported. The prepared catalyst was characterized by elemental analysis, FT-IR and diffuses reflectance UV-Vis spectroscopic methods. This new heterogenized catalyst was found as efficient and reusable catalyst for tetrahydropyranylation of primary, secondary and tertiary alcohols as well as phenols at room temperature.

Acid-washed bentonite: A new reagent for the deprotection of tetrahydropyranyl ethers

Acid-washed (pH 4 and pH 6) bentonite earth cleaves the tetrahydropyranyl ethers to the corresponding alcohols in good yield under mild conditions.