{"id":77955,"date":"2018-03-09T23:23:34","date_gmt":"2018-03-09T23:23:34","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/sa%c2%adntesis-enantioselectiva-de-aminoalcoholes-biologicamente-activos-mediante-apertura-regioselectiva-de-epoxidos-insaturados\/"},"modified":"2018-03-09T23:23:34","modified_gmt":"2018-03-09T23:23:34","slug":"sa%c2%adntesis-enantioselectiva-de-aminoalcoholes-biologicamente-activos-mediante-apertura-regioselectiva-de-epoxidos-insaturados","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica\/sa%c2%adntesis-enantioselectiva-de-aminoalcoholes-biologicamente-activos-mediante-apertura-regioselectiva-de-epoxidos-insaturados\/","title":{"rendered":"S\u00edntesis enantioselectiva de aminoalcoholes biol\u00f3gicamente activos mediante apertura regioselectiva de ep\u00f3xidos insaturados"},"content":{"rendered":"<h2>Tesis doctoral de <strong> Caterina Murruzzu <\/strong><\/h2>\n<p>En la presente tesis doctoral se ha presentado una nueva aproximaci\u00f3n sint\u00e9tica a la s\u00edntesis de aminopolioles biol\u00f3gicamente activos a partir de ep\u00f3xidos insaturados. Se ha propuesto una metodolog\u00eda para la obtenci\u00f3n de aminoaz\u00facares con estructura de pirrolidina polihidroxilada, partiendo del (2r, 3r)-2,3-expoxipenten-1-ol. La apertura de este \u00faltimo con un nucle\u00f3filo nitrogenado y la reacci\u00f3n de ring-closing metathesis han permitido obtener un intermedio clave, utilizando en la s\u00edntesis de dos compuestos: el 1,4-didesoxi-1,4-imino-d-alitol y el 1,4-didesoxi-1,4-imino-d-ribitol. Se ha propuesto la primera s\u00edntesis de la desoximanojirimicina marcada isot\u00f3picamente con 13c sobre 3 \u00e1tomos de carbono. La s\u00edntesis se ha empezado con la reacci\u00f3n de acoplamiento del alcohol al\u00edlico correspondiente, sustrato de la epoxidaci\u00f3n de sharpless. En tan s\u00f3lo 10 pasos ha sido posible obtener el producto final, empleando una metodolog\u00eda previamente optimizada en nuestro grupo de investigaci\u00f3n. Actualmente se est\u00e1n llevando a cabo experimentos de resonancia magn\u00e9tica nuclear para conocerla estructura del inhibidor en el sitio activo de la enzima. Se han explorado diversas v\u00edas de acceso a nuevos compuestos con potencial actividad  como inhibidores de glicosidasas, funcionalizados con una amina secundaria, mediante sustituciones al\u00edlicas catalizadas por paladio sobre el intermedio clave empleado tambi\u00e9n en la s\u00edntesis de la desoximanojirimicina. Se ha obtenido con excelentes resultados la swainsonina, uno de los m\u00e1s importante inhibidores de glicosidasa. La s\u00edntesis se basa en la utilizaci\u00f3n del mismo intermedio clave utilizado en la s\u00edntesis de la desoximanojirimicina. La reacciones clave han sido la expoxidaci\u00f3n de sharpless, para introducir la quiralidad; la reacci\u00f3n de ring-closing metathesis, parala formaci\u00f3n dela estructura c\u00edclia y la dihidroxilaic\u00f3n asim\u00e9trica, parala introducci\u00f3n delos grupos hidroxilo del producto final. Se ha intenta<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>S\u00edntesis enantioselectiva de aminoalcoholes biol\u00f3gicamente activos mediante apertura regioselectiva de ep\u00f3xidos insaturados<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 S\u00edntesis enantioselectiva de aminoalcoholes biol\u00f3gicamente activos mediante apertura regioselectiva de ep\u00f3xidos insaturados <\/li>\n<li><strong>Autor:<\/strong>\u00a0 Caterina Murruzzu <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Barcelona<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 19\/12\/2005<\/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>Antoni Riera Escal\u00e9<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: josep Font cierco <\/li>\n<li>amadeu Llebaria soldevila (vocal)<\/li>\n<li>miquel Peric\u00ed\u00a0s brondo (vocal)<\/li>\n<li>Francisco ram\u00f3n Sarabia Garc\u00eda (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Caterina Murruzzu En la presente tesis doctoral se ha presentado una nueva aproximaci\u00f3n sint\u00e9tica a la s\u00edntesis [&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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