{"id":42710,"date":"1999-11-02T00:00:00","date_gmt":"1999-11-02T00:00:00","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/n-bencil-23-o-isopropiliden-d-gliceraldehido-nitrona-bign-aplicaciones-en-sintesis-organica\/"},"modified":"1999-11-02T00:00:00","modified_gmt":"1999-11-02T00:00:00","slug":"n-bencil-23-o-isopropiliden-d-gliceraldehido-nitrona-bign-aplicaciones-en-sintesis-organica","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica\/n-bencil-23-o-isopropiliden-d-gliceraldehido-nitrona-bign-aplicaciones-en-sintesis-organica\/","title":{"rendered":"N-bencil-2,3-o-isopropiliden-d-gliceraldehido nitrona (bign): aplicaciones en sintesis organica."},"content":{"rendered":"<h2>Tesis doctoral de <strong>  Castillo De Casas Elena <\/strong><\/h2>\n<p>Gran parte de los productos naturales y de otros de notable importancia biol\u00f3gica contienen en su estructura un \u00e1tomo de nitr\u00f3geno. Adem\u00e1s, la actividad biol\u00f3gica de las mol\u00e9culas org\u00e1nicas \u00f3pticamente activas est\u00e1 invariablemente relacionada con su pureza enantiom\u00e9rica. Por todo ello el empleo de bloques sint\u00e9ticos quirales que lleven incorporado un \u00e1tomo de nitr\u00f3geno es de gran utilidad en la s\u00edntesis de compuestos enantiom\u00e9ricamente puros, uno de los retos de la qu\u00edmica org\u00e1nica actual.  en esta memoria se describe el estudio acerca del comportamiento de la n-bencil nitrona derivada de 2,3-o-isopropiliden-d-gliceraldeh\u00eddo (bign) como tal bloque sint\u00e9tico.  en primer lugar se aborda el estudio de las adiciones nucle\u00f3filas, concretamente de organomagnesianos, a fin de constatar el rendimiento y diastereoselectividad de dicha reacci\u00f3n. Se ensayaron organomagnesianos de fenilo, metilo, etilo y vinilo, encontr\u00e1ndose altas diastereoselectividades y, lo que es m\u00e1s importante, la posibilidad de invertir la misma mediante la utilizaci\u00f3n de et2aici como \u00e1cido de lewis.  a continuaci\u00f3n se describe la transformaci\u00f3n de las hidroxilaminas obtenidas en productos de gran inter\u00e9s sint\u00e9tico y\/o biol\u00f3gico. As\u00ed, en el tercer cap\u00edtulo describimos la obtenci\u00f3n de 3-amino-1,2-dioles enantiom\u00e9ricamente puros, utilizando como intermedios de reacci\u00f3n las correspondientes aminas protegidas. Posteriormente, y a partir de estos 3-amino-1,2-dioles, se lleva a cabo la s\u00edntesis de (2r-3s)-n-terc-butoxicarbonil-3-fenilisoserina y de su ep\u00edmero (2s,3s). Estos alfa-hidroxi-beta-amino\u00e1cidos son de gran inter\u00e9s puesto que son estereois\u00f3meros de la cadena lateral del taxoteretm.  en el cap\u00edtulo iv se presenta una nueva metodolog\u00eda que permite la s\u00edntesis de d- y l-n-hidroxi-alfa-amino\u00e1cidos partiendo de \u00fanico sustrato quiral, la nitrona bign objeto de estudio en esta memoria. Esta s\u00edntesis enantiodivergente se<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>N-bencil-2,3-o-isopropiliden-d-gliceraldehido nitrona (bign): aplicaciones en sintesis organica.<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 N-bencil-2,3-o-isopropiliden-d-gliceraldehido nitrona (bign): aplicaciones en sintesis organica. <\/li>\n<li><strong>Autor:<\/strong>\u00a0  Castillo De Casas Elena <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Zaragoza<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 11\/02\/1999<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n<h3>Direcci\u00f3n y tribunal<\/h3>\n<ul>\n<li><strong>Director de la tesis<\/strong>\n<ul>\n<li>Pedro Merino Filella<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: jose Fuentes mota <\/li>\n<li>Miguel Carda uso (vocal)<\/li>\n<li>pedro Molina (vocal)<\/li>\n<li>daniel Carmona gascon (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Castillo De Casas Elena Gran parte de los productos naturales y de otros de notable importancia biol\u00f3gica [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"","ast-site-content-layout":"","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","theme-transparent-header-meta":"","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"default","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"var(--ast-global-color-4)","background-image":"","background-repeat":"repeat","background-position":"center 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