- Stereoselective Epimerizations of Glycosyl Thiols
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Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective β-d-manno- and β-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.
- Doyle, Lisa M.,O'Sullivan, Shane,Di Salvo, Claudia,McKinney, Michelle,McArdle, Patrick,Murphy, Paul V.
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p. 5802 - 5805
(2017/11/10)
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- Studies on the conformational flexibility of α-l-rhamnose-containing oligosaccharides using 13C-site-specific labeling, NMR spectroscopy and molecular simulations: Implications for the three-dimensional structure of bacterial rhamnan polysaccha
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Bacterial polysaccharides are comprised of a variety of monosaccharides, l-rhamnose (6-deoxy-l-mannose) being one of them. This sugar is often part of α-(1 → 2)- and/or α-(1 → 3)-linkages and we have therefore studied the disaccharide α-l-Rhap-(1 → 2)-α-l
- Jonsson, K. Hanna M.,Saewen, Elin,Widmalm, Goeran
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p. 2453 - 2463
(2012/04/23)
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- Synthesis of Oligosaccharides Corresponding to the Common Polysaccharide Antigen of Group B Streptococci
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To facilitate mapping of the immunodominant region of the common polysaccharide antigen of group B streptococci, tetrasaccharide 1-O--α-rhamnopyranosyl>-D-glucitol (2) was synthesized in a stepwise fasion
- Pozsgay, Vince,Jennings, Harold J.
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p. 4042 - 4052
(2007/10/02)
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