Development of a new glycosidation method to obtain 2-deoxy-beta-glycosides, and study of syntheses of the trisaccharide chain in the aureolic acid.
Item
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Title
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Development of a new glycosidation method to obtain 2-deoxy-beta-glycosides, and study of syntheses of the trisaccharide chain in the aureolic acid.
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Identifier
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AAI9917643
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identifier
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9917643
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Creator
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Dios, M. Angeles.
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Contributor
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Adviser: Richard W. Franck
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Date
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1999
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Language
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English
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Publisher
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City University of New York.
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Subject
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Chemistry, Organic | Chemistry, Biochemistry
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Abstract
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Part 1. An innovative method for the syntheses of 2-Deoxy-beta-glycosides was developed. A bicyclic glycosyl donor was formed through a hetero Diels-Alder reaction. This 1,4 oxathiin system formed in the Diels-Alder reaction was used to obtain a disaccharide through conventional activation in the presence of a suitable acceptor. Reduction of the sulfur at C2 of the donor unit in the disaccharide by treatment with Ra-Ni produced 2- deoxy-glycosides in good yield. Studies on the novel stereoelectronic behavior of the bicyclic glycosyl donors were conducted.;Part 2. The glycosidation method developed in part 1 was applied to a study of the syntheses of the trisaccharide unit present in the aureolic acid. Several cycloadducts were synthesized and the stereoselectivity of hetero Diels-Alder reactions was studied.
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Type
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dissertation
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Source
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PQT Legacy CUNY.xlsx
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degree
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Ph.D.
