Abstract
Heparan sulfate (HS), ubiquitously distributed on the cell surface and the extracellular matrix, plays significant roles in biological systems. A 3-O-sulfated HS octasaccharide was identified to bind with the glycoprotein D of herpes simplex virus type-1. This dissertation aims on the development of a strategy for the synthesis of this octasaccharide. The monosaccharide building blocks 16, 17 and 18 were prepared from diacetone D-glucose, D-glucosamine, and D-glucopyranosyl pentaacetate in six, eghit, and six steps, respectively. Assembly of these monosaccharide synthons followed by stereoselective glycosidation and a series of regioselective deprotection yielded the disaccharide building blocks 10 and 14. Coupling of compounds 14 and 15 gave the trisaccharide 11, which underwent glycosidation with the disaccharide 10 to afford the desired pentasaccharide skeleton 54. Anticipately, this pentasaccharide 54 can be coupled with another trisaccharide unit to provide the octasaccharide skeleton.