Stereochemical studies of the synthesis of α-amino-nitriles related to lincosamine (cas 13006-69-4)☆

Add time:08/30/2019    Source:sciencedirect.com

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 occurred at C-6 and the resulting aminonitriles were formed under thermodynamic control. From these chain extensions, precursors of lincosamine and analogues were obtained.

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