ABSTRACT

Glycoside synthesis is a very common reaction in nature, thus providing a great variety of compounds, such as various types of oligosaccharides, or glycoconjugates with lipids (glycolipids), with proteins (glycoproteins or proteoglycans), and with many other naturally occurring compounds. The important biological implications of the attachment of sugar moieties and especially of complex oligosaccharide structures to an aglycon are only now becoming more and more obvious, thus creating a growing general interest in the field [l-7]. The great structural variety available to sugars [la] complicates the synthesis of glycosides and, even more so, of complex oligosaccharide structures. It has only recently become possible to develop methods for the synthesis of such complex compounds [l-4]. The results obtained in this endeavor are summarized in Scheme 1, which will be shortly discussed; however, the main emphasis in this chapter will be devoted to the tri-

Scheme 1

chloroacetimidate method, which has become a very competitive, widely applicable procedure for glycoside bond formation (1,4].