Author, as appears in the article.: Mestre J., Collado D., Benito-Alifonso D., Rodríguez M., Matheu M., Díaz Y., Castillón S., Boutureira O.
Department: Química Analítica i Química Orgànica
URV's Author/s: Castillón Miranda, Sergio / Díaz Giménez, María Yolanda / Matheu Malpartida, María Isabel
Keywords: Oxocarbenium ions Oxidation Molecular mechanical investigations Glycosides Glycals Furanoses Enables access Digitoxin Cations 2-deoxyglycosides
Abstract: 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.
Thematic Areas: 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
licence for use: https://creativecommons.org/licenses/by/3.0/es/
ISSN: 20462069
Author's mail: yolanda.diaz@urv.cat maribel.matheu@urv.cat sergio.castillon@urv.cat
Author identifier: 0000-0001-5567-8108 0000-0001-5216-9260 0000-0002-0690-7549
Last page: 30079
Record's date: 2024-09-07
Journal volume: 8
Papper version: info:eu-repo/semantics/publishedVersion
Link to the original source: https://pubs.rsc.org/en/content/articlelanding/2018/ra/c8ra06619a#!divAbstract
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Papper original source: Rsc Advances. 8 (53): 30076-30079
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
Article's DOI: 10.1039/c8ra06619a
Entity: Universitat Rovira i Virgili
Journal publication year: 2018
First page: 30076
Publication Type: Journal Publications
Repositori URV