Syntheses of derivatives of L-tolyposamine and L-forosamine

Abstract

Methyl 4-benzamido-2,3,4,6-tetradeoxy-α-L-erythro-hexopyranoside (methyl N-benzoyl-α-L-tolyposaminide)(6) and methyl 2,3,4,6-tetradeoxy-4-dimethylamino-α-erythro-hexopyranoside (methyl α-L-forosaminide)(7) have been synthesized by way of an iodide displacement on the allylic sulphonate, methyl 2,3,6-trideoxy-4-O-methylsulphonyl-α-L-erythro-hex-2-enopyranoside (3), followed by an azide displacement on the resulting iodide (4).