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Strathprints serves world leading Open Access research by the University of Strathclyde, including research by the Strathclyde Institute of Pharmacy and Biomedical Sciences (SIPBS), where research centres such as the Industrial Biotechnology Innovation Centre (IBioIC), the Cancer Research UK Formulation Unit, SeaBioTech and the Centre for Biophotonics are based.

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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.