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.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6454400 | PMC |
| http://dx.doi.org/10.1021/acs.joc.9b00022 | DOI Listing |
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