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2,3-Aziridino Ribofuranosyl Donors in Glycoside Bond Synthesis

  • Author / Creator
    Ahmed, Md. Faiaz
  • 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.

  • Subjects / Keywords
  • Graduation date
    2013-06
  • Type of Item
    Thesis
  • Degree
    Master of Science
  • DOI
    https://doi.org/10.7939/R34H7X
  • License
    This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.
  • Language
    English
  • Institution
    University of Alberta
  • Degree level
    Master's
  • Department
    • Department of Chemistry
  • Supervisor / co-supervisor and their department(s)
    • Lowary, Todd L. (Chemistry)
  • Examining committee members and their departments
    • West, Frederick G. (Chemistry); Rivard, Eric (Chemistry)