Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 7, Pages 4486-4500Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00022
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Funding
- NWO-VENI grant
- ERC-STG grant [758913]
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Stereoselective glycosylation remains the main challenge in the chemical synthesis of oligosaccharides. Herein we report a simple method to convert thioglycosides into beta-sulfonium ions via an intramolecular alkylation reaction, leading to highly alpha-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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