172847-89-1Relevant articles and documents
α-Selective Glycosylation with β-Glycosyl Sulfonium Ions Prepared via Intramolecular Alkylation
Moons, Sam J.,Mensink, Rens A.,Bruekers, Jeroen P. J.,Vercammen, Maurits L. A.,Jansen, Laura M.,Boltje, Thomas J.
, p. 4486 - 4500 (2019)
Stereoselective glycosylation remains the main challenge in the chemical synthesis of oligosaccharides. Herein we report a simple method to convert thioglycosides into β-sulfonium ions via an intramolecular alkylation reaction, leading to highly α-selective glycosylations for a variety of glycosyl acceptors. The influence of the thioglycoside substituent and the protecting group pattern on the glycosyl donor was investigated and showed a clear correlation with the observed stereoselectivity.