SYNTHESIS OF 1-ARYL-(GLYCOFURANO)IMIDAZOLIDINE-2-THIONES FROM NEW 2-(ALKYLAMINO)-2-DEOXYHEXOSES

Article abstract of DOI:10.1016/0008-6215(84)85305-7

The new amino sugars 2-deoxy-2-(ethylamino)-α-L-glucopyranose, 2-deoxy-2-(propylamino)-α-L-glucopyranose, and 2-deoxy-2-(ethylamino)-α(or β)-L-mannopyranose have been prepared from L-arabinose by the aminonitrile synthesis.The reaction between these aminohexoses and aryl isothiocyanates affords the corresponding 3-alkyl-1-aryl-(1,2-dideoxy-α-L-glucofurano)<2,1-d>imidazolidine-2-thiones and 3-alkyl-1-aryl-(1,2-dideoxy-β-L-mannofurano)<2,1-d>imidazolidine-2-thiones.The structures of the new compounds described were elucidated by chemical and physical methods.