Synthesis of 3-Deoxy-Β-Mannosides with 3-Deoxy-3-Thio Donors and Subsequent Desulfurization

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Programme Social programme Plenary speakers Keynote speakers 1st EuroCarb Young Researcher (ECYR) Workshop CarboMet Workshop Mini symposium: Glycobiology at the LUMC and beyond Favourites/Agenda

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1st EuroCarb Young Researcher (ECYR) Workshop

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Mini symposium: Glycobiology at the LUMC and beyond

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Synthesis of 3-Deoxy-Β-Mannosides with 3-Deoxy-3-Thio Donors and Subsequent Desulfurization

Tim McMillan 1 , David Crich 1

1 Wayne State University, Detroit, United States

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

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