Autor según el artículo: Mestre, Jordi; Collado, David; Benito-Alifonso, David; Rodriguez, Miguel A; Isabel Matheu, M; Diaz, Yolanda; Castillon, Sergio; Boutureira, Omar
Departamento: Química Analítica i Química Orgànica
Autor/es de la URV: Boutureira Martín, Omar / Castillón Miranda, Sergio / Díaz Giménez, María Yolanda / Matheu Malpartida, María Isabel
Palabras clave: Oxocarbenium ions Oxidation Molecular mechanical investigations Glycosides Glycals Furanoses Enables access Digitoxin Cations 2-deoxyglycosides
Resumen: The preparation of well-defined D-xylo and D-ribo glycosides represents a synthetic challenge due to the limited configurational availability of starting materials and the laborious synthesis of homogeneous 2-deoxy-β-glycosidic linkages, in particular that of the sugar-steroid motif, which represents the "stereoselective determining step" of the overall synthesis. Herein we describe the use of 2-deoxy-2-iodo-glycopyranosyl sulfoxides accessible from widely available D-xylose and D-ribose monosaccharides as privileged glycosyl donors that permit activation at very low temperature. This ensures a precise kinetic control for a complete 1,2-trans stereoselective glycosylation of particularly challenging steroidal aglycones.
Áreas temáticas: Zootecnia / recursos pesqueiros Saúde coletiva Química Odontología Medicina veterinaria Medicina iii Medicina ii Medicina i Materiais Interdisciplinar Geociências General chemistry General chemical engineering Farmacia Ensino Engenharias iv Engenharias iii Engenharias ii Engenharias i Economia Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências ambientais Ciências agrárias i Ciência de alimentos Ciência da computação Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemical engineering (miscellaneous) Chemical engineering (all) Biotecnología Biodiversidade Astronomia / física
Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
ISSN: 20462069
Direcció de correo del autor: omar.boutureira@urv.cat yolanda.diaz@urv.cat maribel.matheu@urv.cat sergio.castillon@urv.cat
Identificador del autor: 0000-0002-0768-8309 0000-0001-5567-8108 0000-0001-5216-9260 0000-0002-0690-7549
Página final: 30079
Fecha de alta del registro: 2024-11-30
Volumen de revista: 8
Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
Referencia al articulo segun fuente origial: Rsc Advances. 8 (53): 30076-30079
Referencia de l'ítem segons les normes APA: Mestre, Jordi; Collado, David; Benito-Alifonso, David; Rodriguez, Miguel A; Isabel Matheu, M; Diaz, Yolanda; Castillon, Sergio; Boutureira, Omar (2018). Highly reactive 2-deoxy-2-iodo-D-allo and D-gulopyranosyl sulfoxide donors ensure ß-stereoselective glycosylations with steroidal aglycones. Rsc Advances, 8(53), 30076-30079. DOI: 10.1039/c8ra06619a
Entidad: Universitat Rovira i Virgili
Año de publicación de la revista: 2018
Página inicial: 30076
Tipo de publicación: Journal Publications
Repositori URV