Articles producció científica> Química Analítica i Química Orgànica

Highly reactive 2-deoxy-2-iodo-D-allo and D-gulopyranosyl sulfoxide donors ensure ß-stereoselective glycosylations with steroidal aglycones

  • Dades identificatives

    Identificador: imarina:5133166
    Autors:
    Mestre J., Collado D., Benito-Alifonso D., Rodríguez M., Matheu M., Díaz Y., Castillón S., Boutureira O.
    Resum:
    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.
  • Altres:

    Autor segons l'article: Mestre J., Collado D., Benito-Alifonso D., Rodríguez M., Matheu M., Díaz Y., Castillón S., Boutureira O.
    Departament: Química Analítica i Química Orgànica
    Autor/s de la URV: Castillón Miranda, Sergio / Díaz Giménez, María Yolanda / Matheu Malpartida, María Isabel
    Paraules clau: Oxocarbenium ions Oxidation Molecular mechanical investigations Glycosides Glycals Furanoses Enables access Digitoxin Cations 2-deoxyglycosides
    Resum: 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.
    Àrees temàtiques: 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
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 20462069
    Adreça de correu electrònic de l'autor: yolanda.diaz@urv.cat maribel.matheu@urv.cat sergio.castillon@urv.cat
    Identificador de l'autor: 0000-0001-5567-8108 0000-0001-5216-9260 0000-0002-0690-7549
    Pàgina final: 30079
    Data d'alta del registre: 2024-09-07
    Volum de revista: 8
    Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
    Enllaç font original: https://pubs.rsc.org/en/content/articlelanding/2018/ra/c8ra06619a#!divAbstract
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referència a l'article segons font original: Rsc Advances. 8 (53): 30076-30079
    Referència de l'ítem segons les normes APA: Mestre J., Collado D., Benito-Alifonso D., Rodríguez M., Matheu M., Díaz Y., Castillón S., Boutureira O. (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
    DOI de l'article: 10.1039/c8ra06619a
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2018
    Pàgina inicial: 30076
    Tipus de publicació: Journal Publications
  • Paraules clau:

    Chemical Engineering (Miscellaneous),Chemistry (Miscellaneous),Chemistry, Multidisciplinary
    Oxocarbenium ions
    Oxidation
    Molecular mechanical investigations
    Glycosides
    Glycals
    Furanoses
    Enables access
    Digitoxin
    Cations
    2-deoxyglycosides
    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
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