{"id":14746,"date":"2018-03-09T09:01:34","date_gmt":"2018-03-09T09:01:34","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/sintesis-de-analogos-de-calcitriol-modificados-en-c-18-y-de-metabolitos-de-vitamina-d3-hidroxilados-en-c-24\/"},"modified":"2018-03-09T09:01:34","modified_gmt":"2018-03-09T09:01:34","slug":"sintesis-de-analogos-de-calcitriol-modificados-en-c-18-y-de-metabolitos-de-vitamina-d3-hidroxilados-en-c-24","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica\/sintesis-de-analogos-de-calcitriol-modificados-en-c-18-y-de-metabolitos-de-vitamina-d3-hidroxilados-en-c-24\/","title":{"rendered":"Sintesis de analogos de calcitriol modificados en c-18 y de metabolitos de vitamina d3 hidroxilados en c-24"},"content":{"rendered":"<h2>Tesis doctoral de <strong> Ivan Cornella Taracido <\/strong><\/h2>\n<p>Mediante una reacci\u00f3n de funcionalizaci\u00f3n remota fotoqu\u00edmica de la posici\u00f3n c-18 de un biciclo cd esteroidal, asistidapor un hidroxilo en la posici\u00f3n c-20, se han sintetizado la (8b)-8-[(terc-bultildimetilsilil)oxi]des-a,b-18-yodo-pregnan-20-ona. a partir de este compuesto, se ha preparado el (1a,3b,5z,7e)-18-(3-hidroxi-3-metilbutil)-20-metil-9,10-secopregna-5,7,10(19),20-tetraeno-1,3-diol, mediante una reacci\u00f3n de adici\u00f3n conjugada en presencia de par zn(cu) y con radiaci\u00f3n ultras\u00f3nica. Este es el primer an\u00e1logo de calcitriol con una cadena hidroxilada, similar a la natural, unida a la posici\u00f3n c-18.  se ha sintetizado el (1a,3b,5z,7e,20r)-18,20-epoxi-21-nor-9,10-secocolesta-5,7,10(19)-trien-1,3,25-triol,primer analogo de calcitriol que presenta un puente \u00e9ter entre las posiciones c-18 y c-20, limitando los grados de libertad de la cadena lateral, y al mismo tiempo, situando un \u00e1tomo de ox\u00edgeno pr\u00f3ximo a dicha cadena.  mediante reacci\u00f3n de adici\u00f3n conjugada inducida por ultrasonidos de un yoduro primario que contiene el biciclo cd esteroidal sobre una r-dioxolanona a,b-insaturada, se ha obtenido el compuesto de adici\u00f3n conjugada (2 \u00c2\u00bfr, 5\u00c2\u00bfe,8b)-23-[2\u00c2\u00bf-(terc-butil)-4\u00c2\u00bf-oxo-1\u00c2\u00bf,3\u00c2\u00bf-dioxolan-5\u00c2\u00bf-il]-des-a,b-24-norcolan-8-ol en un exceso diastereomerico del 83%. De manera similar, partiendo de una s-dioxolanona a, b-insaturada, se ha obtenido el compuesto de adici\u00f3n conjugada (2\u00c2\u00bfs,5\u00c2\u00bfe,8b)-23-[2\u00c2\u00bf-(terc-butil)-4\u00c2\u00bf-oxo-1\u00c2\u00bf,3\u00c2\u00bf-dioxolan-5\u00c2\u00bf-il]-des-a,b-24-norcolan-8-ol en un exceso diastereom\u00e9rico del 86%.  a partir de estos dos compuestos se han sintetizado, por primera vez de forma convergente y con elevadas diastereoselectivas, los metabolitos de la vitamina d3 24-hidroxilados: 24r,25-dihidroxivitamina d3 o secalciferol, 1a,24r,25-trihidroxivitamina d3, y24s,25-dihidroxivitamina d3.<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>Sintesis de analogos de calcitriol modificados en c-18 y de metabolitos de vitamina d3 hidroxilados en c-24<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 Sintesis de analogos de calcitriol modificados en c-18 y de metabolitos de vitamina d3 hidroxilados en c-24 <\/li>\n<li><strong>Autor:<\/strong>\u00a0 Ivan Cornella Taracido <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 A coru\u00f1a<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 18\/12\/2001<\/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> Sarandeses Da Costa Luis Alberto<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: Antonio Mouri\u00f1o mosquera <\/li>\n<li>jean-louis Luche (vocal)<\/li>\n<li>Antonio Abad somovilla (vocal)<\/li>\n<li>  (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Ivan Cornella Taracido Mediante una reacci\u00f3n de funcionalizaci\u00f3n remota fotoqu\u00edmica de la posici\u00f3n c-18 de un biciclo [&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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