N-Substituted derivatives of 23-amino-4',23-dideoxymycaminosyl tylonolide. Synthesis and antibacterial activity.

23-Amino-4',23-dideoxymycaminosyl tylonolide diethyl acetal (5) has been prepared from 4',23-dideoxy-23-iodomycaminosyl tylonolide diethyl acetal (3) by treatment with sodium azide followed by selective reduction of the resulting azide (4). 23-Acylamino-23-deoxy (6 approximately 8) and 23-deoxy-23-urethane-type compounds (12 approximately 15) were further prepared. Treatment of the 23-alkylamino-4',23-dideoxymycaminosyl tylonolides (9, 10) with chloroformates gave 23-N-alkyl-23-deoxy-23-urethane-type compounds (16 approximately 21, 29, 30). 23-N-Alkyl-23-deoxy-23-(2-hydroxyethalamino and 2-methoxyethylamino)-4',23-dideoxymycaminosyl tylonolides (22 approximately 25, 27, 28) were prepared from 3 and the corresponding amines. Antibacterial activities and toxicities (for 23 and 27) of these compounds are described. toxicities (for 23 and 27) of these compounds are described.