Synthesis and Coupling Reactions of Cyclopropyl Glycosides

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Description: Carbohydrates are increasingly appreciated for their critical roles in biological functions. It is essential to develop methods with which to synthesize diverse carbohydrates, and glycosidation is a key reaction. We have been investigating the synthesis of cyclopropyl glycosides and their use as donors in the synthesis of disaccharides as well as glycosyl amino acids. Cyclopropyl glycosides were synthesized by two methods in this research. In one method, a vinyl glycoside was synthesized from a mixed acetal and cyclopropanated by the Simmons-Smith reaction. Alternatively, cyclopropanols were obtained by the Kulinkovich reaction and glycosidated by the trichloroacetimidate (TCA) method of Schmidt. These novel glycosyl donors were then coupled to various amino acid and monosaccharide acceptors. The effects of varying levels of substitution on the cyclopropyl ring of the glycosyl donor were observed and compared with donor activity.
Language: English
Format: Degree Work