65042-30-0

Upstream product

• 18458-71-4 cis-2,6-diphenyltetrahydro-4H-pyran-4-one 
• 18458-72-5 trans-2,6-diphenyltetrahydro-4H-pyran-4-one 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 100-52-7 benzaldehyde 
• 74854-90-3 2,6-diphenyl-tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate 
• 25830-20-0 cis-2,6-Diphenyl-4-acetoxy-1-oxacyclohexan 

Downstream Products

• 18458-72-5 trans-2,6-diphenyltetrahydro-4H-pyran-4-one 
• 18458-71-4 cis-2,6-diphenyltetrahydro-4H-pyran-4-one 
• 74854-90-3 2,6-diphenyl-tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate 
• 1470003-89-4 9-(2,6-diphenyltetrahydro-2H-pyran-4-yl)-9H-purin-6-amine 
• 74854-75-4 N-((2R,4R,6S)-2,6-Diphenyl-tetrahydro-pyran-4-yl)-acetamide 
• 74854-71-0 t-2,t-6-diphenyl-r-4-aminooxane 

Relevant academic research and scientific papers

Bismuth triflate catalyzed prins-type cyclization in ionic liquid: Synthesis of 4-tetrahydropyranol derivatives

The reaction of aldehydes with homoallylic alcohols in the presence of catalytic amount of bismuth triflate in [bmim]PF6generates 4-tetrahydropyranol derivatives in excellent yield and with high diastereoselectivity.

Cellulose-SO3H as a recyclable catalyst for the synthesis of tetrahydropyranols via prins cyclization

Tetrahydropyranols are prepared in good yields and with high cis-selectivity by means of the Prins cyclization using cellulose-sulfonic acid under mild reaction conditions. This is the first report on the preparation of tetrahydropyranols using epoxides and homoallylic alcohols via Prins cyclization.

Montmorillonite clay catalyzed in situ Prins-type cyclisation reaction

Homoallylic alcohols smoothly undergo cross-coupling reactions with aldehydes on the surface of montmorillonite clay to generate 4-hydroxy-2,6-disubstituted tetrahydropyrans in high yields with high diastereoselectivity.

Synthesis and anticancer activities of novel guanylhydrazone and aminoguanidine tetrahydropyran derivatives

In this paper we present the convenient syntheses of six new guanylhydrazone and aminoguanidine tetrahydropyran derivatives 2-7. The guanylhydrazone 2, 3 and 4 were prepared in 100% yield, starting from corresponding aromatic ketones 8a-c and aminoguanidi

Microwave-assisted stereospecific synthesis of novel tetrahydropyran adenine isonucleosides and crystal structures determination

We describe in this article stereospecific syntheses for new isonucleosides analogs of adenine 5-7 from tosyl derivatives 2-4 accessing by microwave irradiations (50-80%). The adenine reacts entirely at the N(9) position. Compounds 2-4 were prepared in two steps from the corresponding alcohols 1, 8 and 9 (81-92%). These tetrahydropyrans alcohols 1, 8 and 9 are achiral (Meso compounds) and were prepared in two steps with complete control of 2,4,6-cis relative configuration by Prins cyclization reaction (60-63%) preceded by the Barbier reaction between allyl bromide with benzaldehyde, 4-fluorobenzaldehyde and 2-naphthaldehyde respectively under Lewis acid conditions (96-98%). The configurations and preferential conformations of 5-7 were determined by crystal structure of 6. These novel isonucleosides 5-7 present in silico potentiality to act as GPCR ligand, kinase inhibitor and enzyme inhibitor, evaluated by Molinspiration program, consistent with the expected antiviral and anticancer bioactivities.

Diastereoselective syntheses via Prins cyclization, crystal structures determination and theoretical studies of cis-2,6-diphenyl-4- hydroxytetrahydropyran and analogues

We report in this article the diastereoselective syntheses of tetrahydropyranyl derivatives 1-5, its cis configurational ascertainment by spectroscopy and finally the crystal structures determination that unequivocally shows the 1-5 configurations and its

Efficient,highly diastereoselective MS 4 A-promoted one-pot,three-component synthesis of 2,6-disubstituted-4- tosyloxytetrahydropyrans via Prins cyclization

A simple,efficient and highly diastereoselective one-pot three-component synthesis of functionalized 2,6-disubstituted-4-tosyloxytetrahydropyrans was performed. The synthesis features an optimized Prins cyclization in which an aromatic homoallylic alcohol

The 'aqueous' Prins cyclization: A diastereoselective synthesis of 4-hydroxytetrahydropyran derivatives

Phosphomolybdic acid (H3PMo12O40, a heteropoly acid) is found to catalyze efficiently the Prins cyclization of homoallylic alcohols with aldehydes in water at room temperature to provide tetrahydropyran-4-ol derivatives in high yields with all cis-selectivity. Only cyclic ketones can give spirocyclic products. The use of phosphomolybdic acid in water makes this procedure simple, more convenient, cost-effective, and environmentally friendly. Georg Thieme Verlag Stuttgart.

Amberlyst-15-catalyzed novel synthesis of tetrahydropyranols

The cross-coupling reaction of homoallyl alcohols with aldehydes in the presence of Amberlyst-15 resulted in the formation of 4-hydroxy-2,6-disubstituted tetrahydropyrans in high yields with high diastereoselectivity. The stereochemistry of these products was assigned with the assistance of coupling constants and nOe studies.