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Record identifier : 566161
Personal Name - Primary Intelectual Responsibility : Rodebaugh, Robert
Title and statement of responsibility : I. n-Pentenyl glycosides as probes into the reactivity of the anomeric center. II. The synthesis of nodulation factors. III. Studies directed toward the synthesis of a carbohydrate library [Thesis]
Publication, Distribution,Etc. : Duke University, 1997
Language of the Item : eng
Dissertation of thesis details and type of degree : Ph.D.
Body granting the degree : , Duke University
Summary or Abstract : I. n-Pentenyl glycosides as probes into the reactivity of the anomeric center. n-Pentenyl glycosides (NPGs) have proven to be valuable tools in mechanistic investigations of the forces that influence the reactivity and stereoselectivity of glycosylation. A study of several $\omega$-alkenyl glycosides provided evidence for: (a) the exclusive reactivity of pentenyl glycosides toward oxidative hydrolysis and (b) the significance of intermolecular Br$\sp+$ transfer from a cyclic bromonium ion to an alkene during electrophilic brominations. A solvation-assisted model for the prediction of reactivity trends at the anomeric center was developed using n-pentenyl glucosides as the experimental method and solvation modified activation energies. A study of the parameters of solvent, Lewis acid promoter, and halonium source on NPG glycosidations with steroidal acceptors showed the marked effect these factors may have on anomeric selectivity in the product..
Topical Name Used as Subject : Organic chemistry
Information of biblio record : TL
 
 
 
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