Synthesis of C-glycosides via Ramberg-Backlund reaction.
Item
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Title
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Synthesis of C-glycosides via Ramberg-Backlund reaction.
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Identifier
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AAI3063868
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identifier
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3063868
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Creator
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Pasetto, Paolo Maria.
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Contributor
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Adviser: Richard W. Franck
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Date
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2002
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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
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Abstract
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C-glycosides have attracted much attention as analogs of O-glycosides in which the hydrolytically labile acetal moiety of the sugar is substituted with a functionality more stable toward acids, bases and enzymes. A variety of C-glycosides can also be found in natural products.;The Ramberg-Backlund reaction is a classical method, the novel application to carbohydrate was developed in our laboratory. It has proved to be a valuable synthetic tool to the preparation of C-glycosides due to its high yields, the easy access of the thioglycoside starting materials and the simple reaction conditions.;We applied the Ramberg-Backlund reaction to two research projects, the first of which was the synthesis of C-glycosylated porphyrins as potential agents for photodynamic therapy, proposing an efficient synthetic strategy, which allowed us to prepare hydrolytically stable sugar porphyrins in high yields.;The second project was the synthesis of the northwest quadrant of Altromycin B, an unusual natural C-glycoside, which we see as an interesting and challenging problem in the employment of the Ramberg-Backlund reaction. The comparison of our model compounds with the spectroscopic data of Altromycin B didn't give definitive proof of the relative stereochemistry at the quaternary center in the northwest quadrant.
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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.
