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

Session: 
PS2 Poster session 2 Even numbers
Code: 
P150
Location (hall): 
Foyer
Start/end time: 
Tuesday, July 2, 2019 - 15:45 to 17:15
Tim
McMillan

Tim McMillan1, David Crich1

1Wayne 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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