This thesis is based on four publications. The first chapter describes preparation of anomerically pure thioethyl-, thiophenyl-, and n-pentenyl 2-azido-2-deoxy glycosyl building blocks from easily accessible per-acetylated glycosamines.
In the second part, acetylated, benzylated and non-protected n-pentenyl glycosides are used as substrates for preparing various spacer functionalities, which are obtained by means of radical elongations, oxidations and reductions.
The syntheses of a trisaccharide,a-D-GlcpNAc-(1-->4)-b-D-Galp-(1-->4)-b-D-GlcpNAc, and fragments thereof, linked to a long lipophilic aglycon, are described in the third part. For the formation of theb-D-Galp-(1-->4)-D-GlcpNAc bond, several differently protected glucosamine acceptors were prepared and their reactivity towards a disaccharide donor evaluated.
Finally, lactosamine derivatives were prepared by regioselective galactosylation and used as building blocks in the chemical synthesis of various oligosaccharides. The syntheses of polylactosamine di-, tri- and tetramers were achieved by regioselective glycosylation. Also spacer containing sulfated N-acetyllactosamine and Lewis x structures were synthesised.
Stockholm: Stockholm University , 1999. , 73 p.