Dehydrative Glycosylation in Water Using a Bronsted Acid-Surfactant-Combined Catalyst

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概要

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• Brønsted acid–surfactant-combined catalyst, dodecylbenzenesulfonic acid (DBSA), was used in catalytic dehydrative glycosylation reactions in water. 1-Hydroxy sugars, such as <I>O</I>-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-<FONT SIZE="-2">D</FONT>-ribofuranose showed that hydrophobicity of the substrates was important to attain higher yields. Regarding the α/β selectivities, <FONT SIZE="-2">D</FONT>-ribose and <FONT SIZE="-2">D</FONT>-mannose derivatives gave the products in high β- and α-selectivities, respectively.

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公益社団法人 日本化学会 | 論文

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