STEREOCHEMICAL STUDIES OF THE SYNTHESIS OF α-AMINONITRILES RELATED TO LINCOSAMINE

Article abstract of DOI:10.1016/0008-6215(88)80010-7

The syntheses of 6-amino-6-deoxyheptopyranurononitriles related to lincosamine by cyano-amination of 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose (2) is reported.The procedure described allowed direct cyano-amination in good yield under mild conditions.The high diastereofacial selectivity of the reaction is discussed.Indirect cyano-amination by activation of the corresponding cyanohydrins followed by displacement with an amine was also studied.Epimerization occured at C-6 and the resulting aminonitriles were formed under thermodynamic control.From these chain extensions, precursors of lincosamine and analogues were obtained.