69413-95-2

Upstream product

• 172950-21-9 di-tert-butyl ((1S,3R,4S,5S,6R)-4-(((2S,3R,4S,5S,6R)-4-((tert-butoxycarbonyl)amino)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)amino)-6-(((tert-butoxycarbonyl)methyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate) 
• 119783-93-6 4',2''-di-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-5-epi-1,3,2',6',3''-penta-N-tosylkanamycin B 
• 78788-44-0 4'',6''-O-cyclohexylidene-3'-deoxy-5-epi-1,3,2',6',3''-penta-N-tosylkanamycin B 
• 119783-95-8 4',2''-di-O-acetyl-4'',6''-O-cyclohexylidene-5,3'-dideoxy-5-fluoro-1,3,2',6',3''-penta-N-tosylkanamycin B 

Downstream Products

• 172950-27-5 C₃₃H₆₀FN₅O₁₄ 
• 118811-72-6 C₄₄H₅₃F₄N₅O₁₅ 

Relevant academic research and scientific papers

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

Synthesis of 5-deoxy-5-fluoro and 5-deoxy-5,5-difluoro derivatives of kanamycin B and its analogs. Study on structure-toxicity relationships

5-Deoxy-5-fluoro- (1), 5,3'-dideoxy-5-fluoro- (2), and 5,3',4'-trideoxy-5-fluoro-kanamycin B (3) have been prepared by treatment of 5-epihydroxyl precursors (prepared by the Mitsunobu reaction) with DAST as the key step. 5,3'-Dideoxy-5,5-difluoro- (26) an