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dc.contributor.authorYang, Hai
dc.date.accessioned2014-03-04T02:25:27Z
dc.date.available2014-03-04T02:25:27Z
dc.date.issued2006-08
dc.identifier.otheryang_hai_200608_ms
dc.identifier.urihttp://purl.galileo.usg.edu/uga_etd/yang_hai_200608_ms
dc.identifier.urihttp://hdl.handle.net/10724/23568
dc.description.abstractIn this study, three generations of chiral auxiliary are synthesized and attached to glucose and galactose. The donors containing these chiral auxiliary are synthesized and glycosylations with a variety of glycosyl acceptors are conducted. The glycosylation results showed that a glycosyl donor substituted with a chiral auxiliary can be employed for the stereoselective introduction of 1, 2-cis glycosides such as ±-glucosides and ±-galactosides. The neighboring group participation by the chiral auxiliary leads to a quasi-stable anomeric sulfonium ion, which due to steric and electronic factors, is formed as a trans-decalin ring system. Displacement of the sulfonium ion by a glycosyl acceptor leads to the stereoselective formation of ±-glycosides. The use of this new method in combination with traditional neighboring group participation by esters to introduce ²-glycosides makes it possible to synthesize a wide variety of complex carbohydrates with complete anomeric control.
dc.languageeng
dc.publisheruga
dc.rightspublic
dc.subjectChiral Auxiliary
dc.subjectGlycosylations
dc.subject1
dc.subject2-cis Glycosides
dc.subjectNeighboring Group Participation
dc.subjectCarbohydrate
dc.titleStereoselective glycosylations via chiral auxiliaries
dc.typeThesis
dc.description.degreeMS
dc.description.departmentChemistry
dc.description.majorChemistry
dc.description.advisorGeert-Jan Boons
dc.description.committeeGeert-Jan Boons
dc.description.committeeGeorge Majetich
dc.description.committeeRobert Phillips


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