Syntheses of derivatives of 2,6-diamino-2,3,4,6-tetradeoxy-D-erythro-hexose (purpurosamine C), a component of gentamycin C1a

Abstract

Two routes have been used to synthesize methyl 2,6-diacetamido-2,3,4,6-tetradeoxy-α-D-erythro-hexopyranoside (methyl NN′-diacetyl-α-purpurosaminide C)(13), a derivative of a component sugar of gentamicin C1a. The first route was based on a previous synthesis of DL-(13), whereas the alternative route relied on an azide displacement reaction of methyl 3,4-dideoxy-2,6-bis-O-methylsulphonyl-α-D-threo-hex-3-enopyranoside (19).