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Synlett 1997; 1997(7): 818-820
DOI: 10.1055/s-1997-5762
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Solvent and Other Effects on the Stereoselectivity of Thioglycoside Glycosidations

Alexei Demchenko, Thomas Stauch, Geert-Jan Boons*
  • *School of Chemistry, The University of Birmingham, Edgbaston, Birmingham B15 2TT, UK, Fax: +121 414 4403; email: gjboons@chemistry.bham.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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Iodonium-ion mediated glycosidation of thioglycosides in toluene/1,4-dioxane gives much higher α-selectivities than the use of conventional glycosylation solvents. Furthermore, it is shown that the iodonium-ion source, concentration and presence of molecular sieves have also a major effect on the stereochemical outcome of a glycosylation.

thioglycosides - anomeric selectivity - glycosylation - solvent