A New Method for the Synthesis of 2,3-Aziridino-2,3-dideoxyhexonamides and Their Conversion into 3-Amino-2,3-dideoxyhexonic Acids

Abstract

Two new 2,3-aziridino-2,3-dideoxyhexonamides 3 and 11 were prepared by a three-step procedure from commercially available D-glucono-1,5-lactone and D-gulono-1,4-lactone, respectively. The lactones were converted into methyl 3,4:5,6-di-O-isopropylidene-2-O-mesyl esters 2 and 10, which upon treatment with ammonia formed the title aziridino compounds. These were reductively cleaved by hydrazine to give 3-amino-2,3dideoxyhexonic hydrazides 13 and 15, which were easily converted into the corresponding lactone 14 and acid 16, respectively.