Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 36, Pages 8053-8063Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201905576
Keywords
activation; carbohydrates; glycosylation; glycosyl chlorides; silver oxide
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Funding
- NSF [CHE-1800350]
- National Institute of General Medical Sciences [GM111835]
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Following our discovery that silver(I) oxide-promoted glycosylation with glycosyl bromides can be greatly accelerated in the presence of catalytic TMSOTf or TfOH, we report herein a new discovery that glycosyl chlorides are even more effective glycosyl donors under these reaction conditions. The developed reaction conditions work well with a variety of glycosyl chlorides. Both benzoylated and benzylated chlorides have been successfully glycosidated, and these reaction conditions proved to be effective in coupling substrates containing nitrogen and sulfur atoms. Another convenient feature of this glycosylation is that the progress of the reaction can be monitored visually; its completion can be judged by the disappearance of the characteristic dark color of Ag2O.
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