SUBSTITUTIONS D'ESTERS ALLYLIQUES: PREPARATION DE GLYCALS AMINES EN C-3 ET ETUDE DE LEUR GLYCOSIDATION ACIDO-CATALYSEE. APPLICATION A L'HEMISYNTHESE DE GLYCOSIDES DU GROUPE DES ANTHRACYCLINES

Article abstract of DOI:10.1016/S0008-6215(00)83831-8

3-Amino-1,5-anhydro-2,3,6-trideoxy-L-arabino- and -L-ribo-hex-1-enitol were prepared by substitution of the allylic ester function of 1,5-anhydro-3,4-di-O-benzoyl-2,6-dideoxy-L-arabino-hex-1-enitol with sodium azide, followed by reduction with lithium aluminium hydride.Glycosidation was performed with various alcohols, in particular daunomycinone.In the latter case, the partial synthesis of 4'-epi- and 3',4'-epi-daunorubicines was accomplished in three major steps.