Carbohydrates play major roles in many biological processes. Therefore, the synthesis of oligosaccharides is of considerable interest for biological, medicinal, and pharmacological studies. Many approaches have been developed for the synthesis of oligosaccharides, in which the main focus is often the formation of the glycosidic bonds. Traditional approaches use protecting group strategies that can be time consuming and can result in poor overall yield. This thesis describes the protecting group-free synthesis of a series of glycosyl donors of a range of mono- and disaccharides. These donors can be used to synthesize unprotected glycosyl chlorides, observed in situ. Reaction of the glycosyl chlorides with a variety of nucleophiles afforded the expected displacement products, giving access to a range of O-, N-, and S-linked glycosides, without resorting to the use of protecting groups.

Carbohydrates play major roles in many biological processes. Therefore, the synthesis of oligosaccharides is of considerable interest for biological, medicinal, and pharmacological studies. Many approaches have been developed for the synthesis of oligosaccharides, in which the main focus is often the formation of the glycosidic bonds. Traditional approaches use protecting group strategies that can be time consuming and can result in poor overall yield. This thesis describes the protecting group-free synthesis of a series of glycosyl donors of a range of mono- and disaccharides. These donors can be used to synthesize unprotected glycosyl chlorides, observed in situ. Reaction of the glycosyl chlorides with a variety of nucleophiles afforded the expected displacement products, giving access to a range of O-, N-, and S-linked glycosides, without resorting to the use of protecting groups.