Synthesis of 3', 4'-Dideoxybutirosin A, Active against Butirosin Resistant Bacteria

Synthesis of aminotrideoxybutirosin A, a chemically modified antibiotic active against butirosin-resistant bacteria.

5"-Amino-3',4'5"-trideoxybutirosin A (4) was synthesized by two routes starting from the known tri-O-acetyl-tetra-N-benzyloxycarbonyl-3",5"-O-cyclohexylidene-3',4'-di-O-mesylbutirosin A (5). Introduction of amino function at C-5" was carried out by displacement of 5"-tosyloxy group with sodium azide either before or after 3',4'-deoxygenation. Compound 4 shows outstanding activities against stra...

Synthesis of 3"-epi-dihydrostreptomycin active against resistant bacteria.

Synthesis of 3'-deoxy-3'-fluorokanamycins A and B active against resistant bacteria.

Sir: Kanamycins are inactivated by enzymes of resistant bacteria phosphorylating or adenylylating the 3', 4' or 2"-hydroxyl groups' 21 , among which the 3'-hydroxyl group is most frequently modified. Syntheses of 3'-deoxykanamycin A3), 3',4'-dide-oxykanamycin B4) (dibekacine), and other deoxy derivatives of kanamycins and related aminogly-coside antibiotics were the major solution"" in order to...

Synthesis of 3',4'-dideoxy and 3',4',5''-trideoxyribostamycin active against kanamycin-resistant E. coli and P. aeruginosa.

cin B2) and S'^-dideoxyneamine^ have confirmed that removal of the hydroxyl group which is phosphorylated by drug-resistant bacteria from kanamycins gives compounds active against the resistant organisms. As an extension of this work, we describe in this paper the syntheses of two deoxy-derivatives of ribostamycin4). If inactivation of ribostamycin by Escherichia coli K12-ML 1629 and K12-ML 163...

Synthesis of 5''-amino-3,5''-dideoxybutirosin A.

The titled compound was prepared by condensation of 3'-deoxyparomamine derivative (5) with 2,3-O-bis(p-nitrobenzoyl)-5-O-tosyl-D-xylofuranosyl bromide followed by 1-N-acylation with the active ester of (S)-4-benzyloxycarbonylamino-2-hydroxybutyric acid. The compound was slightly more active than 3'-deoxybutirosin A against Pseudomonas.