Glycosylation of 'basic' alcohols: methyl 6-(hydroxymethyl) picolinate as a case study

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Shuai Wang, Dominique Lafont, Jani Rahkila, Benjamin Picod, Reko Leino, Sébastian Vidal
Publisher: ELSEVIER SCI LTD
Publication year: 2013
Journal: Carbohydrate Research
Journal acronym: CARBOHYD RES
Volume number: 372
Start page: 35
End page: 46
Number of pages: 12
ISSN: 0008-6215


Abstract

Glycosylation is promoted by acid promoters rendering the reactions with basic acceptors challenging. This report presents an in depth study involving methyl 6-(hydroxymethyl) picolinate as the model acceptor and 22 glycosyl donors to afford the desired glycosides in good yields ranging from 46% to 85%. Several parameters were evaluated, including the protecting groups of the glycosyl donor, the leaving group at the anomeric center, and the promoter. The influence of the pyridine ring was evident with a benzene-based acceptor affording high yields of glycoside (79%) in comparison to the pyridine-based acceptor (46%). The present work provides a general and reliable access to pyridine-containing glycosides. (C) 2013 Elsevier Ltd. All rights reserved.


Keywords

Carbohydrate, Glycoside, Glycosylation, Pyridine acceptor, Trichloroacetimidate

Last updated on 2019-07-12 at 02:57