Browsing by Author "Doyle, Lisa M."
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Influence of acyl groups on glucopyranoside reactivity in Lewis acid promoted anomerisation
Farrell, Mark P.; Doyle, Lisa M.; Murphy, Paul V. (Elsevier, 2018-05-26)Lewis acid promoted anomerisation has potential in O- or S-glycoside synthesis. Herein, the anomerisation kinetics of thirty-one β-d-glucopyranosides was determined to determine how particular acyl protecting groups and ... -
Lewis acid promoted anomerisation of alkyl O- and S-xylo-, arabino- and fucopyranosides
Doyle, Lisa M.; Meany, Fiach B.; Murphy, Paul V. (Elsevier, 2018-11-24)Pentopyranoside and 6-deoxyhexopyranosides, such as those from d-xylose, l-arabinose and l-fucose are components of natural products, oligosaccharides or polysaccharides. Lewis acid promoted anomerisation of some of their ... -
Stereoselective epimerizations of glycosyl thiols
Doyle, Lisa M.; O'Sullivan, Shane; Di Salvo, Claudia; McKinney, Michelle; McArdle, Patrick; Murphy, Paul V. (American Chemical Society, 2017-10-17)Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while ... -
Studies in anomerisation of glycosyl thiols and glycosides
Doyle, Lisa M. (NUI Galway, 2018-06-29)The stereoselective generation of 1,2-cis linkages continues to be a substantial challenge in carbohydrate chemistry today. Lewis acid-promoted anomerisation of 1,2-trans linkages offers a facile method to generate 1,2-cis ...