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Open Access research with a European policy impact...

The Strathprints institutional repository is a digital archive of University of Strathclyde's Open Access research outputs. Strathprints provides access to thousands of Open Access research papers by Strathclyde researchers, including by researchers from the European Policies Research Centre (EPRC).

EPRC is a leading institute in Europe for comparative research on public policy, with a particular focus on regional development policies. Spanning 30 European countries, EPRC research programmes have a strong emphasis on applied research and knowledge exchange, including the provision of policy advice to EU institutions and national and sub-national government authorities throughout Europe.

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Intramolecular 1,8-hydrogen-atom transfer reactions in (1 -> 4)-o-disaccharide systems: conformational and stereochemical requirements

Francisco, C.G. and Herrera, A.J. and Kennedy, A.R. and Martin, A. and Melian, D. and Perez-Martin, I. and Quintanal, L.M. and Suarez, E. (2008) Intramolecular 1,8-hydrogen-atom transfer reactions in (1 -> 4)-o-disaccharide systems: conformational and stereochemical requirements. Chemistry - A European Journal, 14 (33). pp. 10369-10381. ISSN 0947-6539

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Abstract

The stereochemical and conformational factors controlling the intramolecular hydrogen-atom transfer (HAT) reaction between the two pyranose units in a (14)-O-disaccharide when promoted by a primary 6-O-yl radical are studied. Models with -D-Glcp-(14)--D-Glcp, -L-Rhamp-(14)--D-Galp or -D-Manp-(14)--L-Gulp skeletons led exclusively to the abstraction of the hydrogen from HC-5 and the formation, through a nine-membered transition state, of a 1,3,5-trioxocane ring system in a stable boat-chair conformation. Notwithstanding, derivatives of -L-Rhamp-(14)--D-Glcp or -D-Manp-(14)--D-Galp exclusively abstract the hydrogen from HC-1 through a seven-membered transition state and, therefore, lead to an interglycosidic spiro ortho ester.