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Literature on the Synthesis and Chemistry of Carbohydrate Thiiranes

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Literature on the Synthesis and Chemistry of Carbohydrate Thiiranes CARBOHYDRATE MANIPULATIONS TOWARDS HIGH-MANNOSE OLIGOSACCHARIDES Javier Castilla López Dipòsit Legal: T.1214-2012 ADVERTIMENT. L'accés als continguts d'aquesta tesi doctoral i la seva utilització ha de respectar els drets de la persona autora. Pot ser utilitzada per a consulta o estudi personal, així com en activitats o materials d'investigació i docència en els termes establerts a l'art. 32 del Text Refós de la Llei de Propietat Intel·lectual (RDL 1/1996). Per altres utilitzacions es requereix l'autorització prèvia i expressa de la persona autora. En qualsevol cas, en la utilització dels seus continguts caldrà indicar de forma clara el nom i cognoms de la persona autora i el títol de la tesi doctoral. No s'autoritza la seva reproducció o altres formes d'explotació efectuades amb finalitats de lucre ni la seva comunicació pública des d'un lloc aliè al servei TDX. Tampoc s'autoritza la presentació del seu contingut en una finestra o marc aliè a TDX (framing). Aquesta reserva de drets afecta tant als continguts de la tesi com als seus resums i índexs. ADVERTENCIA. El acceso a los contenidos de esta tesis doctoral y su utilización debe respetar los derechos de la persona autora. Puede ser utilizada para consulta o estudio personal, así como en actividades o materiales de investigación y docencia en los términos establecidos en el art. 32 del Texto Refundido de la Ley de Propiedad Intelectual (RDL 1/1996). Para otros usos se requiere la autorización previa y expresa de la persona autora. En cualquier caso, en la utilización de sus contenidos se deberá indicar de forma clara el nombre y apellidos de la persona autora y el título de la tesis doctoral. No se autoriza su reproducción u otras formas de explotación efectuadas con fines lucrativos ni su comunicación pública desde un sitio ajeno al servicio TDR. Tampoco se autoriza la presentación de su contenido en una ventana o marco ajeno a TDR (framing). Esta reserva de derechos afecta tanto al contenido de la tesis como a sus resúmenes e índices. WARNING. Access to the contents of this doctoral thesis and its use must respect the rights of the author. It can be used for reference or private study, as well as research and learning activities or materials in the terms established by the 32nd article of the Spanish Consolidated Copyright Act (RDL 1/1996). Express and previous authorization of the author is required for any other uses. In any case, when using its content, full name of the author and title of the thesis must be clearly indicated. Reproduction or other forms of for profit use or public communication from outside TDX service is not allowed. Presentation of its content in a window or frame external to TDX (framing) is not authorized either. These rights affect both the content of the thesis and its abstracts and indexes. UNIVERSITAT ROVIRA I VIRGILI CARBOHYDRATE MANIPULATIONS TOWARDS HIGH-MANNOSE OLIGOSACCHARIDES Javier Castilla López Dipòsit Legal: T.1214-2012 UNIVERSITAT ROVIRA I VIRGILI CARBOHYDRATE MANIPULATIONS TOWARDS HIGH-MANNOSE OLIGOSACCHARIDES Javier Castilla López Dipòsit Legal: T.1214-2012 UNIVERSITAT ROVIRA I VIRGILI CARBOHYDRATE MANIPULATIONS TOWARDS HIGH-MANNOSE OLIGOSACCHARIDES Javier Castilla López Dipòsit Legal: T.1214-2012 JAVIER CASTILLA LÓPEZ CARBOHYDRATE MANIPULATIONS TOWARDS HIGH-MANNOSE OLIGOSACCHARIDES DOCTORAL THESIS Supervised by Dra. Yolanda Díaz Giménez and Dr. Sergio Castillón Miranda Departament de Química Analítica i Química Orgànica Tarragona, 2012 UNIVERSITAT ROVIRA I VIRGILI CARBOHYDRATE MANIPULATIONS TOWARDS HIGH-MANNOSE OLIGOSACCHARIDES Javier Castilla López Dipòsit Legal: T.1214-2012 UNIVERSITAT ROVIRA I VIRGILI CARBOHYDRATE MANIPULATIONS TOWARDS HIGH-MANNOSE OLIGOSACCHARIDES Javier Castilla López Dipòsit Legal: T.1214-2012 Departament de Química Analítica i Química Orgànica Facultat de Química c/ Marcel·lí Domingo, s/n 43007, Tarragona Els sotasignants Sergio Castillón Miranda, Catedràtic de Química Orgànica, i Yolanda Díaz Giménez, Professora Titular de Química Orgànica, del Departament de Química Analítica i Química Orgànica de la Universitat Rovira i Virgili, FEM CONSTAR que aquesta memòria, titulada Carbohydrate manipulations towards high-mannose oligosaccharides, que presenta en Javier Castilla López per optar al grau de Doctor en Química per la Universitat Rovira i Virgili, ha estat realitzada sota la nostra direcció al Departament de Química Analítica i Química Orgànica d’aquesta universitat, així com en d’altres laboratoris universitaris en el marc d’una sèrie de col·laboracions científiques i que, a més, compleix els requeriments per poder optar a la Menció Europea. Tarragona, 14 de juny de 2012 Dr. Sergio Castillón Miranda Dra. Yolanda Díaz Giménez UNIVERSITAT ROVIRA I VIRGILI CARBOHYDRATE MANIPULATIONS TOWARDS HIGH-MANNOSE OLIGOSACCHARIDES Javier Castilla López Dipòsit Legal: T.1214-2012 UNIVERSITAT ROVIRA I VIRGILI CARBOHYDRATE MANIPULATIONS TOWARDS HIGH-MANNOSE OLIGOSACCHARIDES Javier Castilla López Dipòsit Legal: T.1214-2012 La present memòria de Tesi Doctoral s’ha dut a terme gràcies al Programa de Formación del Profesorado Universitario (referència: AP2007-03782), finançat pel Ministerio de Ciencia e Innovación. La realització d’aquesta Tesi Doctoral ha estat possible gràcies al finançament dels següents projectes d’investigació: - Síntesis de monómeros, oligómeros, dendrímeros y polímeros derivados de carbohidratos con propiedades antibióticas y antivirales (CTQ2005-03124- BQU) - New synthetic methods in carbohydrate chemistry (CTQ2008-01569-BQU) - Diseño de Catalizadores para una Química Sostenible: Una Aproximación Integrada. Consolider Ingenio 2010 - Proyecto INTECAT (CSD2006-0003) UNIVERSITAT ROVIRA I VIRGILI CARBOHYDRATE MANIPULATIONS TOWARDS HIGH-MANNOSE OLIGOSACCHARIDES Javier Castilla López Dipòsit Legal: T.1214-2012 UNIVERSITAT ROVIRA I VIRGILI CARBOHYDRATE MANIPULATIONS TOWARDS HIGH-MANNOSE OLIGOSACCHARIDES Javier Castilla López Dipòsit Legal: T.1214-2012 CONTRIBUCIONS A CONGRESSOS Castilla, J.; Cruz, D.; Rísquez, R.; Ortiz Mellet, C.; García Fernández, J. Díaz, Y.; Castillón, S. Carbohydrate-based 1,3-oxazoline-2-thiones: from synthesis to biological applications. 26th International Carbohydrate Symposium. Comunicació flash F61. Madrid, 2012. Castilla, J. Synthesis and biological evaluations of 1,3-oxazoline-2-thione-sugar derivatives. CEICS Nobel Campus - Chemistry for life. Comunicació oral. Tarragona, 2012. Castilla, J.; Cruz, D.; Rísquez, R.; Ortiz Mellet, C.; García Fernández, J. Díaz, Y.; Castillón, S. Bicyclic pyranose―2-alkylsulfanyl-1,3-oxazoline glycomimetics: Conformationally- locked N-glycosides with selective β-glucosidase inhibitory activity. CEICS Nobel Campus - Chemistry for life. Pòster. Tarragona, 2012. Castilla, J.; Cruz, D.; Rísquez, R.; Ortiz Mellet, C.; García Fernández, J. Díaz, Y.; Castillón, S. Synthesis, derivatization and biological evaluation of 1,3-oxathiolan-2-imine- carbohydrate derivatives. 16th European Carbohydrate Symposium. Pòster PO 53. Sorrento-Nàpols, 2011. Díaz, Y.; Marín, I.; Castilla, J.; Matheu, M. I.; Castillón, S. Synthetic transformations from gycal epoxides. X Jornadas de Carbohidratos. Reunión del Grupo Especializado de Hidratos de Carbono de la RSEQ. Comunicació convidada IL 6. Granada, 2010. Castilla, J.; Cruz, D.; Matheu, M. I.; Díaz, Y.; Castillón, S. Synthesis and derivatization of 1,2-oxycarbonimidoylthio-sugar derivatives. X Jornadas de Carbohidratos. Reunión del Grupo Especializado de Hidratos de Carbono de la RSEQ. Pòster P8. Granada, 2010. Castilla, J.; Marín, I.; Matheu, M. I.; Díaz, Y.; Castillón, S. Síntesi i reaccions de 1,2- anhidrosucres. Síntesi de carbohidrats 1,3-oxatiolan-, 1,3-oxaselenolan- i 1,3-oxazolidin- 2-derivats. VI Trobada de Joves Investigadors dels Països Catalans. Comunicació oral 2.3.1. València, 2010. Castilla, J.; Matheu, M. I.; Díaz, Y.; Castillón, S. Synthesis of 1,2-oxycarbonimidoylthio- sugar derivatives. 15th European Carbohydrate Symposium. Pòster PA 100. Viena, 2009. Castilla, J.; Matheu, M. I.; Díaz, Y.; Castillón, S. Towards the synthesis of glycal- 1,2-episulfides. Synthesis of 1-deoxy-1,2-oxycarbonimidoylthio-sugar derivatives. IV Reunión Química-Orgánica del Mediterráneo, REQOMED. Pòster P-15. Girona, 2008. UNIVERSITAT ROVIRA I VIRGILI CARBOHYDRATE MANIPULATIONS TOWARDS HIGH-MANNOSE OLIGOSACCHARIDES Javier Castilla López Dipòsit Legal: T.1214-2012 Castilla, J.; Matheu, M. I.; Díaz, Y.; Castillón, S. An approach to the synthesis of glycal- 1,2-episulfides. IV Iberian Carbohydrate Meeting. IX Jornadas de Carbohidratos. Pòster P04. Santiago de Compostela, 2008. UNIVERSITAT ROVIRA I VIRGILI CARBOHYDRATE MANIPULATIONS TOWARDS HIGH-MANNOSE OLIGOSACCHARIDES Javier Castilla López Dipòsit Legal: T.1214-2012 PUBLICACIONS Castilla, J.; Rísquez, R.; Cruz, D.; Higaki, K.; Nanba, E.; Ohno, K.; Suzuki, Y.; Díaz, Y.; Ortiz Mellet, C.; García Fernández, J. M., Castillón, S. Conformationally-locked N-glycosides with selective β-glucosidase inhibitory activity: identification of a new pharmacological chaperone for Gaucher disease. J. Med. Chem. 2012, 55, 6857-6865. Marín, I.; Castilla, J.; Matheu, M. I.; Díaz, Y.; Castillón, S. Sequential directed epoxydation-acidolysis from glycals with MCPBA. A flexible approach to protected glycosyl donors. J. Org. Chem. 2011, 76, 9622-9629. Castilla, J.; Marín, I.; Matheu, M. I.; Díaz, Y.; Castillón, S. Short and general procedure for synthesizing cis-1,2-fused 1,3-oxazolidine-2-thione and 2-selone carbohydrate derivatives. J. Org. Chem. 2010, 75, 514-517. Corrigendum J. Org. Chem. 2012,
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