SYNTHESIS OF 1-N-(D-THREO-AND RACEMIC ERYTHRO-3-AMINO2-HYDROXYBUTANOYL)-2', 3'-DIDEOXYKANAMYCIN A

Abstract

1-N-(D-Threo-3-amino-2-hydroxybutanoyl)-2', 3'-dideoxykanamycin A has been prepared by coupling of 3, 6'-bis(N-benzyloxycarbony-2', 3'-dideoxy-3''-N-(trifluoroacetyl)kanamycin A with D-threo-3-azido-2-hydroxybutanoic acid. A diastereomeric mixture of the erythro analog has also been prepared by use of racemic erythro-3-azido-2-hydroxybutanoic acid. Synthesis of the D-threo- and racemic erythro-3-amino-2-hydroxybutanoic acids has been described.