The recent development of stereoselective glycosylations has helped pave the way towards the synthesis of both glycoconjugates and oligosaccharides alike. A notable linkage of such a species is the elusive 1,2-cis linkage, specifically the 1,2-cis linkage in the β-mannose series. These reactions are sensitive to the functionality at the 3-position. In particular, it has been found that the 3-deoxy series gives little to no selectivity. In this presentation we address the limitation through the synthesis of a variety of 3-deoxy-3-thio-substituted mannosyl donors followed by desulfurization. The effects of the different substituents at sulfur on stereoselectivity will be disucssed, as will applications towards biologically relavant oligosaccharides.
General Glycosylation and Subsequent Desulfuriztion of Substrates
