Document Type



Doctor of Philosophy



Date of Defense


Graduate Advisor

Alexei Demchenko


Alexei V. Demchenko, Ph.D

Stephen M. Holmes, Ph.D.

Christopher D. Spilling, Ph.D.

Rudolph E. K. Winter, Ph.D.


Since carbohydrates were first discovered, understanding the structure, reactivity, and function of these bioorganic compounds has remained of great priority. However, as the appreciation for the biological roles of carbohydrates intensifies, a growing demand for efficient and scalable methods towards the synthesis of these challenging molecules has become even more imperative. While modern synthetic techniques have allowed us to readily achieve most glycosidic linkages, it is the inability to effectively predict and control the stereoselectivity of the glycosylation reaction that has remained the synthetic hurdle. Herein, much effort has been placed in the investigation of “mixed-patterned” glycosyl donors as they have shown some interesting behaviors in glycosylation. Initial findings revealed that the behavior of these particular donors could be rationalized by a theory developed in our laboratory, entitled the “O-2/O-5 cooperative effect,” wherein the energetic consequences associated with particular protecting group patterns were analyzed. As a result, the work of this doctoral dissertation is centered upon the exploration of glycosyl donor protecting groups, and their effect on both the reactivity and stereoselectivity with which the glycosylation reaction proceeds.

OCLC Number


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Chemistry Commons