Beilstein J. Org. Chem.2021,17, 964–976, doi:10.3762/bjoc.17.78
covalently bind Lewis basic fluoride ions in a relatively stable fluorosulfite anion (FSO2−). Herein we report the application of liquid SO2 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 O- and S-mannosides, as well as one example of a C-mannoside, are synthesized to demonstrate the scope of the glycosyl acceptors. The formation of the fluorosulfite species
equilibrium.
Keywords: fluorosulfite; glycosyl fluoride; Lewis acid; liquid sulfur dioxide; metal-free glycosylation; Introduction
The glycosylation reaction is still one of the most important and basic synthetic strategies in carbohydrate chemistry that provides access to the various types of
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Graphical Abstract
Scheme 1:
Scope of glycosyl acceptors for glycosylation with pivaloyl-protected mannosyl fluoride α-1a in liq...