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Org. Chem."],"accepted":{"date-parts":[[2021,4,17]]},"abstract":"<jats:p>Liquid SO<jats:sub>2<\/jats:sub> is a polar solvent that dissolves both covalent and ionic compounds. Sulfur dioxide possesses also Lewis acid properties, including the ability to covalently bind Lewis basic fluoride ions in a relatively stable fluorosulfite anion (FSO<jats:sub>2<\/jats:sub><jats:sup>\u2212<\/jats:sup>). Herein we report the application of liquid SO<jats:sub>2<\/jats:sub> as a promoting solvent for glycosylation with glycosyl fluorides without any external additive. By using various temperature regimes, the method is applied for both armed and disarmed glucose and mannose-derived glycosyl fluorides in moderate to excellent yields. A series of pivaloyl-protected <jats:italic>O<\/jats:italic>- and <jats:italic>S<\/jats:italic>-mannosides, as well as one example of a <jats:italic>C<\/jats:italic>-mannoside, are synthesized to demonstrate the scope of the glycosyl acceptors. The formation of the fluorosulfite species during the glycosylation with glycosyl fluorides in liquid SO<jats:sub>2<\/jats:sub> is proved by <jats:sup>19<\/jats:sup>F NMR spectroscopy. A sulfur dioxide-assisted glycosylation mechanism that proceeds via solvent separated ion pairs is proposed, whereas the observed \u03b1,\u03b2-selectivity is substrate-controlled and depends on the thermodynamic equilibrium.<\/jats:p>","DOI":"10.3762\/bjoc.17.78","type":"journal-article","created":{"date-parts":[[2021,4,29]],"date-time":"2021-04-29T14:27:37Z","timestamp":1619706457000},"page":"964-976","source":"Crossref","is-referenced-by-count":14,"title":["Metal-free glycosylation with glycosyl fluorides in liquid 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