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dc.contributor.advisorO'Hagan, David
dc.contributor.authorBresciani, Stefano
dc.coverage.spatial200en_US
dc.date.accessioned2011-06-17T13:08:08Z
dc.date.available2011-06-17T13:08:08Z
dc.date.issued2011-06-22
dc.identifieruk.bl.ethos.552567
dc.identifier.urihttp://hdl.handle.net/10023/1878
dc.description.abstractThis thesis describes stereospecific fluorination reactions, and addresses the synthesis of fluorosugars. In Chapter 1, the influence of fluorine on the physical properties of organic molecules, as well as its stereoelectronic effects, are introduced. Furthermore, an overview of nucleophilic and electrophilic fluorination reactions is given. Chapter 2 describes the dehydroxyfluorination of allylic alcohol diastereoisomers 155a and 155b, which can proceed either by direct or allylic fluorination. The regio- and stereo- selectivities were also assessed. Chapter 3 outlines the synthesis of the novel trifluoro D-glucose analogue 193 and trifluoro D-altrose analogue 216. The transport of these hexose analogues across the red blood cell membranes was then explored, to investigate the influence of polarity versus hydrogen bonding ability in carbohydrate-protein interactions. Chapter 4 describes the development and optimisation of Bio’s methodology, to promote stereospecific dehydroxyfluorination of benzylic alcohols (R)-213 and (R)-227 by addition of TMS-amine additives 226 and 229. And finally Chapter 5 reports the experimental procedures as well as the characterisation and the crystallographic data of the molecules prepared in this thesis.en_US
dc.language.isoenen_US
dc.publisherUniversity of St Andrews
dc.subjectStereospecificen_US
dc.subjectFluorosugarsen_US
dc.subjectFluorinationen_US
dc.subjectBenzylic alcoholen_US
dc.subjectPolarityen_US
dc.subjectHydrogen bonden_US
dc.subjectAllylicen_US
dc.subjectTransporten_US
dc.subjectRed blood cell membraneen_US
dc.subjectFluorineen_US
dc.subjectRegioselectivityen_US
dc.subjectStereoselectivityen_US
dc.subjectTrifluoro D-glucose analogueen_US
dc.subjectTrifluoro D-altrose analogueen_US
dc.subject.lccQD281.F55B8
dc.subject.lcshFluorinationen_US
dc.subject.lcshStereochemistryen_US
dc.subject.lcshMonosaccharides--Derivatives--Synthesisen_US
dc.subject.lcshBiological transporten_US
dc.titleStereospecific dehydroxyfluorination and the synthesis of trifluoro D-hexose sugar analoguesen_US
dc.typeThesisen_US
dc.type.qualificationlevelDoctoralen_US
dc.type.qualificationnamePhD Doctor of Philosophyen_US
dc.publisher.institutionThe University of St Andrewsen_US


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