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

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

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