Catalytic, Regioselective Sulfonylation of Carbohydrates with Dibutyltin Oxide under Solvent-Free Conditions

2021 
A simple approach was developed for the solvent-free regioselective functionalization of carbohydrate polyols with 4-toluesulfonyl (tosyl) group, allowing the easy and quick activation of a saccharide site with a tosylate leaving group. The method is based on the use of catalytic dibutyltin oxide and tetrabuylammonium bromide (TBAB), and a moderate excess of N,N-diisopropylethyl amine (DIPEA) and tosyl chloride (TsCl), leading to the selective functionalization at 75 °C of a secondary equatorial hydroxy function flanked by an axial one in a pyranoside. The procedure is endowed with several advantages, such as the use of cheap reagents, experimental simplicity, and the need for reduced reaction times in comparison with other known approaches.
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