ABSTRACT

The biological relevance of carbohydrates and carbohydrate-containing compounds is increasingly becoming evident. Compounds of this class include glycoamine and macrolide antibiotics, anthracycline and enediyne anticancer antibiotics, and numerous oligosaccharides implicated in cell-cell recognition, cellular-immune response, cell oncogenic transformation and inflammation, and other cell biology phenomena [l]. As glycobiology moves forward, the need for efficient methods to render oligosaccharides available for further investigations becomes more acute. Despite the Jong history of the field, oligosaccharide synthesis lacks behind peptide [2] and oligonucleotide [3] synthesis in terms of efficiency and automation. In this chapter, we will briefly review the main synthesis methods available for glucoside bond formation [4] and then proceed to discuss the twostage activation procedure based on the chemistry of glycosyl fluorides and sulfides.