74854-90-3Relevant academic research and scientific papers
Diastereoselective syntheses via Prins cyclization, crystal structures determination and theoretical studies of cis-2,6-diphenyl-4- hydroxytetrahydropyran and analogues
Silva,Sabino,Martins,Vasconcellos
, p. 478 - 487 (2013)
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
Microwave-assisted stereospecific synthesis of novel tetrahydropyran adenine isonucleosides and crystal structures determination
Silva, Fábio P.L.,Cirqueira, Marilia L.,Martins, Felipe T.,Vasconcellos, Mário L.A.A.
, p. 189 - 196 (2013/10/08)
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.
Efficient,highly diastereoselective MS 4 A-promoted one-pot,three-component synthesis of 2,6-disubstituted-4- tosyloxytetrahydropyrans via Prins cyclization
Ahmed, Naseem,Konduru, Naveen Kumar
, p. 177 - 185 (2012/04/10)
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
Preparation and Stereochemistry of Some Substituted 2,6-Diphenyl-4-aminotetrahydropyrans
Chandrasekrar, Nallappan,Ramalingan, Kondareddiar,Herd, Melvin D.,Berlin, K. Darrell
, p. 4352 - 4358 (2007/10/02)
Four epimeric pairs of 2,6-diphenyl-4-aminooxanes (tetrahydropyrans) have been prepared by the reduction of oximes of 2,6-diphenyl-4-oxanones. Lithium aluminum hydride reduction of oximes affords a mixture of epimeric amines rich in the equatorially subst
