Stereospecific Synthesis of a Dihydroxyethylene Isostere of Cyclohexylalanine Amide, (2S,3R,4S)-4-Amino-5-Cyclohexyl-1-Morpholino-2,3-Pentanediol(ACMP) from a Protected Sugar

ABSTRACT

A transition-state analogue of a renin inhibitor at the scissile site, a dihydroxyethylene isostere of cyclohexylalanine amide, (2S,3R,4S)-4-amino-5-cyclohexyl-1-morpholino-2,3-pentanediol(ACMP), was synthesized from 1,2:5,6-di-O-isopropylidene-α-D-allofuranose stereospecifically.