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: sergio.castillon@urv.cat maribel.matheu@urv.cat yolanda.diaz@urv.cat

Author identifier: 0000-0002-0690-7549 0000-0001-5216-9260 0000-0001-5567-8108

Last page: 30079

Record's date: 2023-02-18

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: http://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