Synthesis and Transformation of Glycosyl Azides

Abstract

Publisher Summary This chapter discusses the synthesis and transformation of glycosyl azides. Owing to their functional group, glycosyl azides constitute important and versatile derivatives for carbohydrate chemistry. Because of the dipole character of organic azides, they can function both as nucleophiles and electrophiles and readily undergo dipolar cycloadditions. In addition, as configurationally stable groups, azides are well suited as starting materials for the formation of other nitrogen-containing functionalities such as amines, amides, ureas, carbodiimides, and others. The only method known up to 1974 for preparing glycosyl azides was from acylated glycosyl halides by the treatment with sodium or silver azide. However, because of the reactivity of glycosyl halides with water, the very low solubility of sodium azide in organic solvents, and the thermal ability of silver azide, there were considerable difficulties in preparing the corresponding glycosyl azides. This chapter discusses the synthesis of 1,2- trans glycosyl azides from glycosyl halides. It also explains the synthesis of 1,2- trans -glycopyranosyl azides by intramolecular rearrangement and elaborates the reduction and oxidation of glycosyl azides.