000065283 001__ 65283
000065283 005__ 20190709135645.0
000065283 0247_ $$2doi$$a10.3390/catal7120393
000065283 0248_ $$2sideral$$a104262
000065283 037__ $$aART-2017-104262
000065283 041__ $$aeng
000065283 100__ $$0(orcid)0000-0002-0136-5138$$aFraile, J.M.$$uUniversidad de Zaragoza
000065283 245__ $$aApplication of heterogeneous catalysts in the first steps of the oseltamivir synthesis
000065283 260__ $$c2017
000065283 5060_ $$aAccess copy available to the general public$$fUnrestricted
000065283 5203_ $$aThe first steps of oseltamivir synthesis from quinic acid involve acetalization and ester formation. These reactions are catalyzed by either acids or bases, which may be accomplished by heterogeneous catalysts. Sulfonic solids are efficient acid catalysts for acetalization and esterification reactions. Supported tetraalkylammonium hydroxide or 1, 5, 7-triazabicyclo[4.4.0]dec-5-ene are also efficient base catalysts for lactone alcoholysis and in this work, these catalysts have been applied in two alternative synthetic routes that lead to oseltamivir. The classical route consists of an acetalization, followed by a lactonization, and then a lactone alcoholysis. This achieves a 66% isolated yield. The alternative route consists of esterification followed by acetalization and is only efficient when an acetone acetal is used.
000065283 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E11$$9info:eu-repo/grantAgreement/ES/MINECO/CTQ2014-52367-R
000065283 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/
000065283 590__ $$a3.465$$b2017
000065283 591__ $$aCHEMISTRY, PHYSICAL$$b55 / 146 = 0.377$$c2017$$dQ2$$eT2
000065283 592__ $$a0.855$$b2017
000065283 593__ $$aPhysical and Theoretical Chemistry$$c2017$$dQ2
000065283 593__ $$aCatalysis$$c2017$$dQ2
000065283 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000065283 700__ $$aSaavedra, C.J.
000065283 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000065283 773__ $$g7, 12 (2017), 393 [14 pp]$$pCatalysts$$tCatalysts$$x2073-4344
000065283 8564_ $$s501039$$uhttps://zaguan.unizar.es/record/65283/files/texto_completo.pdf$$yVersión publicada
000065283 8564_ $$s104897$$uhttps://zaguan.unizar.es/record/65283/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000065283 909CO $$ooai:zaguan.unizar.es:65283$$particulos$$pdriver
000065283 951__ $$a2019-07-09-12:40:34
000065283 980__ $$aARTICLE