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Access Type
WSU Access
Date of Award
January 2024
Degree Type
Dissertation
Degree Name
Ph.D.
Department
Chemistry
First Advisor
Hien Nguyen
Abstract
2-Deoxy glycosides are a highly valuable class of carbohydrates commonly found in biologically active molecules. In natural products, the composition and length of 2-deoxy glycosides often contribute significantly to the potency of these compounds. However, the stereoselective synthesis of this class of carbohydrates is challenging due to their high reactivity and the inability to utilize well-established C2 neighboring group participation for stereoselectivity control. Current methods heavily rely on expensive transition metal and organocatalysts. This work introduces the use of commercially available phenanthroline as an additive for the selective glycosylation of 2-deoxy glycosyl chloride donors. Additionally, it employs an economical source of trifluoromethyl radical, TTCF3OTf, under mild reaction conditions to afford 2-deoxy-2-trifluoromethyl glycosides. These methods provide efficient access to α-2-deoxy and 2-deoxy-2-trifluoromethyl glycosides through operationally simple protocols. Collectively, these approaches demonstrate the feasibility of using commercially available reagents for the synthesis of high-value carbohydrate molecules.
Recommended Citation
English, Connor Kennedy, "Development Of Methods For The Synthesis Of 2-Deoxy Glycosides" (2024). Wayne State University Dissertations. 4093.
https://digitalcommons.wayne.edu/oa_dissertations/4093
