Department of Chemistry, Silesian Technical University, Gliwice, Poland
There is a considerable interest in the synthesis of furanose oligosaccharides and related analogues that could act as either glycosyltransferase substrates or inhibitors. Complex oligosaccharides containing furanose moieties are important constituents of a number of bacteria, fungi and plants.
As a part of our programme directed at the synthesis of furanose oligosaccharides we are interested in developing an efficient route to oligosaccharides with terminal furanosyl moiety.
We present the simple synthesis of benzyl-protected glycofuranoses, starting material for preparation of glycosyl donors (dithiocarbonates, diothiocarbamates, thiocarbamates, phosporodithioates).1 The method of synthesis of glycofuranosyl thioglycosides will be described.2 Condensation of glycosyl donors prepared with thioglycosides under the agency of thiphilic compounds proceeds with high yields and good degrees of 1,2-cis stereoselectivity.
The mechanism of the glycosylation will be presented.
1. J. Bogusiak, W.Szeja, Carbohydr. Res., 295(1990) 235; J.Bogusiak, W.Szeja Synlett 6(1997) 661; J.Bogusiak, I.Wandzik, W.Szeja, Carbohydr.Lett., 1(1996)411; J.Bogusiak, W.Szeja, Carbohydr. Res., 230(2001 141; A.Kasprzycka, Ph.D. Thesis, Gliwice (2004).
2. I.Fokt, J.Bogusiak, W.Szeja Carbohydr.Lett. 3(1998)191.