78740-48-4

Upstream product

• 34493-98-6 dibecacin 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 78740-49-5 4'',6''-O-cyclohexylidene-1,3,2',6',3''-pentakis(N-tert-butoxycarbonyl)dibekacin 
• 173009-70-6 5,3',4'-trideoxy-5-epifluorokanamycin B 
• 119783-91-4 1-N<(S)-4-amino-2-hydroxybutanoyl>-5,3',4'-trideoxy-5-epifluorokanamycin B 
• 189157-26-4 C₅₀H₈₃F₄N₅O₁₉S 
• 189157-23-1 2''-O-acetyl-4'',6''-O-cyclohexylidene-1,3,2',6',3''-pentakis(N-tert-butoxycarbonyl)dibekacin 
• 189157-24-2 2''-O-acetyl-4'',6''-O-cyclohexylidene-5-deoxy-5-epi-5-fluoro-1,3,2',6',3''-pentakis(N-tert-butoxycarbonyl)dibekacin 
• 189157-29-7 4'',6''-O-cyclohexylidene-5,2''-dideoxy-5-epi-5-fluoro-2''-oxo-1,3,2',6',3''-pentakis(N-tert-butoxycarbonyl)dibekacin 
• 189157-25-3 4'',6''-O-cyclohexylidene-5-deoxy-5-epi-5-fluoro-1,3,2',6',3''-pentakis(N-tert-butoxycarbonyl)dibekacin 
• 189157-27-5 2'',3''-O,N-carbonyl-4'',6''-O-cyclohexylidene-5-deoxy-5,2''-diepi-5-fluoro-1,3,2',6'-tetrakis(N-tert-butoxycarbonyl)dibekacin 

Relevant academic research and scientific papers

Synthesis of 2''-oxidized derivatives of 5-deoxy-5-epi-5-fluoro-dibekacin and -arbekacin, and study on structure-chemical shift relationships of urethane(or amide)-type NH protons in synthetic intermediates

Three 2''-modified dibekacin-analogs have been prepared as potential compounds active against resistant bacteria producing 2''-O-phosphotransferases; one is 5-deoxy-5,2''-diepi-5-fluorodibekacin (9) prepared from a suitably protected 2''-O-triflyl derivative through the 2'',3''-cyclic carbamate, and the others are 2''-oxo derivatives (12 and 22, both as the hydrate) of 5-deoxy-5-epi-5-fluoro-dibekacin and -arbekacin prepared through oxidation at C-2'' of suitably protected derivatives. Relationships between the t-butoxycarbonyl(= Boc)-NH-shifts of per-N-Boc synthetic intermediates and their structures were studied. It was found that the shifts, measured in pyridine-d5 at 80 °C, which spread over a close range (δ 6-7 ppm), are sensitively influenced by nearby and surrounding groups around the BocNH group in respect of electron-withdrawing character, hydrogen bonding (BocNH ... acceptor), and also solvent effects (BocNH ... NC5H5).

Synthesis of 5-deoxy-5-epifluoro derivatives of arbekacin, amikacin and 1-N-tobramycin (study on structure - toxicity relationships)

As part of a study on fluorination-toxicity relationships for aminoglycoside antibiotics, 5,3'-dideoxy-5-epifluorokanamycin B (10), 5,3',4'-trideoxy-5-epifluorokanamycin B (11), 1-N--5-deoxy-5-epifluorotobramycin (19), 5-deoxy-5-epifluoroarbekacin (20), and 5-deoxy-5-epifluoroamikacin (21) have been prepared.The acute toxicities of these three 5-deoxy-5-epifluoro compounds showed values almost identical or similar to those for arbekacin (ABK) and amikacin (15), making a sharp contrast with the toxicities of the corresponding 5-deoxy-5-fluoro derivatives.This fact is explained on the basis of basicity changes (retention for the 5-epifluoro derivatives and reduction for the 5-fluoro derivatives) at the H2N-3 groups of the fluorinated compounds compared to the parent compounds; this hypothesis was substantiated by the pKa values at the H3N1+-1,3-groups (determined by the shift changes depending on pD values at C-2 and C-4, 6 in their 13C NMR spectra) of 2,5-dideoxy-5-epifluorostreptamine (23) and 2,5-dideoxy-5-fluorostreptamine (24), chosen as model compounds, and 2-deoxystreptamine (DST). Keywords: Arbekacin; Amikacin; 1-N-(S)-4-Amino-2-hydroxybutanoyl)tobramycin