Dehydrative Glycosylation in Water Using a Brønsted Acid–Surfactant-Combined Catalyst

Abstract

Abstract Brønsted acid–surfactant-combined catalyst, dodecylbenzenesulfonic acid (DBSA), was used in catalytic dehydrative glycosylation reactions in water. 1-Hydroxy sugars, such as O-benzyl-protected furanose and pyranose, reacted with alcohols and a nitrogen nucleophile in the presence of a catalytic amount of DBSA to afford the desired adducts in good yields. Detailed study of the glycosylation of 2-deoxy-d-ribofuranose showed that hydrophobicity of the substrates was important to attain higher yields. Regarding the α/β selectivities, d-ribose and d-mannose derivatives gave the products in high β- and α-selectivities, respectively.