Facile Synthesis of 1,2-trans-Nitrophenyl-1-Thioglycopyranosides

Hugues Driguez; Wieslaw Szeja

doi:10.1055/s-1994-25704

Synthesis 1994; 1994(12): 1413-1414
DOI: 10.1055/s-1994-25704

short paper

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Facile Synthesis of 1,2-trans-Nitrophenyl-1-Thioglycopyranosides

Hugues Driguez^* , Wieslaw Szeja

^*Centre de Recherches sur les Macromolécules Végétales, CNRS, BP 53 X, F-38041 Grenoble Cedex 9, France

Abstract

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1,2-trans-2-Nitro-, 4-nitro- and 2,4-dinitrophenyl-1-thioglycopyranosides were synthesized in high yield by condensation of per-O-acetyl-1-thioglucose with the appropriate nitro- or dinitrofluorobenzene in the presence of potassium carbonate. The pseudothiourea precursor was also used under these coupling conditions. 1,2-trans-4-Nitrophenyl-1-thioglycosides derived from β-D-galactose, β-D-xylose, α-L-arabinose and maltose were also obtained in good yield.

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