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2,3-Aziridino Ribofuranosyl Donors in Glycoside Bond Synthesis Open Access


Other title
Glycosylation method
Type of item
Degree grantor
University of Alberta
Author or creator
Ahmed, Md. Faiaz
Supervisor and department
Lowary, Todd L. (Chemistry)
Examining committee member and department
West, Frederick G. (Chemistry); Rivard, Eric (Chemistry)
Department of Chemistry

Date accepted
Graduation date
Master of Science
Degree level
The number of biologically important events mediated by carbohydrates has generated great interest in the synthesis of oligosaccharides and the development of new methods for glycosidic bond formation. I have developed a glycosylation method where glycosyl donors containing a three-membered epoxide ring are used. These species are highly selective glycosyl donors and the glycoside bonds formed are cis to the epoxide moiety. In this project, I have extended this work to substrates in which the epoxide ring is replaced with an aziridine moiety. For this purpose, I synthesized two aziridine-containing donors N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-D-ribofuranose (1) and N-acetyl-2,3-aziridino-5-O-benzoyl-2,3-dideoxy-β-D-ribofuranosyl trichloroacetimidate (2). A seven step route was developed for the synthesis of hemiacetal (1) starting from D-arabinose and one step is required to synthesize trichloroacetimidate (2) from 1. Glycosylation of a range of alcohol acceptors with donor 1 using dimethylsulfide and trifluoromethanesulfonic acid anhydride (Gin glycoslylation) gave products in good yields and with moderate : selectivity. Glycosylation of these alcohols with 2 promoted by trimethylsilyl trifluoromethanesulfonate proceed with slightly better selectivity. I also investigated the effect of diethyl ether on glycosylation reactions with donor 2.
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