Author, as appears in the article.: Castillón, S. ; Cardona, A. ; Boutureira, O.; Díaz, Y. ; Matheu, M. I.

Department: Química Analítica i Química Orgànica

URV's Author/s: CASTILLÓN MIRANDA, SERGIO; Cardona, A. ; Boutureira, O.; DÍAZ GIMÉNEZ, MARÍA YOLANDA; MATHEU MALPARTIDA, MARÍA ISABEL

Keywords: Supercritial CO2 glycosylation

Abstract: Supercritical carbon dioxide (scCO2) is a suitable medium to perform transition metal-free glycosylations in the absence of volatile organic solvents (VOCs) using glycosyl halides as glycosyl donors. The methodology here described can be applied for obtaining O-glycosides in a totally green reaction, as well as orthoesters, depending on the reaction conditions. The process is much more sensitive to temperature changes than to pressure modification, glycosyl chlorides requiring higher temperatures to be activated than glycosyl bromides. Pivaloyl groups act as good CO2-philic units and showed to be the best choice to obtain good stereoselectivities. The relevance of the fluid nature and supercritical conditions was also evidenced.

Research group: Síntesis Orgànica Estereoselectiva

Thematic Areas: Chemistry Química Química

licence for use: https://creativecommons.org/licenses/by/3.0/es/

ISSN: 1463-9262

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

Record's date: 2018-02-27

Journal volume: 19

Papper version: info:eu-repo/semantics/publishedVersion

Link to the original source: https://pubs.rsc.org/en/content/articlelanding/2017/gc/c7gc00722a#!divAbstract

Funding program: plan; RYC-2015-17705 plan; Excelencia; CTQ2014-58664-R

Article's DOI: 10.1039/c7gc00722a

Entity: Universitat Rovira i Virgili

Journal publication year: 2017

First page: 2687

Publication Type: Article Artículo Article