dc.contributor.author | Doyle, Lisa M. | |
dc.contributor.author | Meany, Fiach B. | |
dc.contributor.author | Murphy, Paul V. | |
dc.date.accessioned | 2021-01-08T10:41:45Z | |
dc.date.available | 2021-01-08T10:41:45Z | |
dc.date.issued | 2018-11-24 | |
dc.identifier.citation | Doyle, Lisa M., Meany, Fiach B., & Murphy, Paul V. (2019). Lewis acid promoted anomerisation of alkyl O- and S-xylo-, arabino- and fucopyranosides. Carbohydrate Research, 471, 85-94. doi:https://doi.org/10.1016/j.carres.2018.11.010 | en_IE |
dc.identifier.issn | 1873-426X | |
dc.identifier.issn | 0008-6215 | |
dc.identifier.uri | http://hdl.handle.net/10379/16434 | |
dc.description.abstract | 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 alkyl O- and S-glycopyranosides is reported here. SnCl4 was more successful than TiCl4, with the latter giving the glycosyl chloride by-product in some cases, and both were superior to BF3OEt2. Kinetics study using 1H NMR spectroscopy showed an order of reactivity: O-xylopyranoside¿>¿O-arabinopyranoside¿>¿O-fucopyranoside. Benzoylated glycosides were more reactive than acetylated glycosides. The reactivity of S-glycosides was greater than that of O-glycosides for both arabinose and fucose derivatives; the reactivity of O- and S-xylopyranosides was similar. The highest stereoselectivities were observed for fucopyranosides. The ß-d-xylopyranoside and ¿-l-arabinopyranoside reactants are conformationally more flexible than ß-l-fucopyranosides. | en_IE |
dc.description.sponsorship | This publication has emanated from research supported by Science Foundation Ireland (SFI, grant number 12/IA/1398) and is co-funded under the European Regional Development Fund under Grant Number 14/SP/2710. | en_IE |
dc.format | application/pdf | en_IE |
dc.language.iso | en | en_IE |
dc.publisher | Elsevier | en_IE |
dc.relation.ispartof | Carbohydrate Research | en |
dc.rights | Attribution-NonCommercial-NoDerivs 3.0 Ireland | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/3.0/ie/ | |
dc.subject | Lewis acid promoted anomerisation | en_IE |
dc.subject | alkyl O- | en_IE |
dc.subject | S-xylo- | en_IE |
dc.subject | arabino- | en_IE |
dc.subject | fucopyranosides | en_IE |
dc.title | Lewis acid promoted anomerisation of alkyl O- and S-xylo-, arabino- and fucopyranosides | en_IE |
dc.type | Article | en_IE |
dc.date.updated | 2021-01-07T08:14:41Z | |
dc.identifier.doi | 10.1016/j.carres.2018.11.010 | |
dc.local.publishedsource | https://doi.org/10.1016/j.carres.2018.11.010 | en_IE |
dc.description.peer-reviewed | peer-reviewed | |
dc.contributor.funder | Science Foundation Ireland | en_IE |
dc.contributor.funder | European Regional Development Fund | en_IE |
dc.internal.rssid | 24261613 | |
dc.local.contact | Paul Murphy, School Of Chemistry, Room 108, Arts/Science Building, Nui Galway. 2465 Email: paul.v.murphy@nuigalway.ie | |
dc.local.copyrightchecked | Yes | |
dc.local.version | ACCEPTED | |
dcterms.project | info:eu-repo/grantAgreement/SFI/SFI Investigator Programme/12/IA/1398/IE/Glycoside & glycoconjugate synthesis through development and application of chelation induced anomerization/ | en_IE |
dcterms.project | info:eu-repo/grantAgreement/SFI/SFI Spokes Programme/14/SP/2710/IE/Gut Inflammation _ Discovery and Therapeutic Targeting of the Secretome-Receptome Inflammatory Network in Inflammatory Bowel Disease/ | en_IE |
nui.item.downloads | 121 | |