1154757-24-0

Basic information

• Product Name: ACHN 490
• Synonyms: ACHN 490;O-2-AMino-2,3,4,6-tetradeoxy-6-[(2-hydroxyethyl)aMino]-α-D-glycero-hex-4-enopyranosyl-(1→4)-O-[3-deoxy-4-C-Methyl-3-(MethylaMino)-β-L-arabinopyranosyl-(1→6)]-N1-[(2S)-4-aMino-2-hydroxy-1-oxobutyl]-2-deoxy-D-streptaMine;PlazoMicin;IYDYFVUFSPQPPV-BPUQVFSTSA-N
• CAS NO: 1154757-24-0
• Molecular Formula: C₂₅H₄₈N₆O₁₀
• Molecular Weight: 592.68282
• Product Categories: Amines;Intermediates & Fine Chemicals;Oligosaccharides;Pharmaceuticals
• Mol File: 1154757-24-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 896.4±65.0 °C(Predicted)
• Appearance: /
• Density: 1.40±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Water (Slightly)
• PKA: 13.11±0.20(Predicted)
• CAS DataBase Reference: ACHN 490(CAS DataBase Reference)
• NIST Chemistry Reference: ACHN 490(1154757-24-0)
• EPA Substance Registry System: ACHN 490(1154757-24-0)

Safety Data

• Hazardous Substances Data: 1154757-24-0(Hazardous Substances Data)

Usage

Uses

Plazomicin is a neoglycoside antibiotic with activity against a broad range of Gram-positive and Gram-negive pathogens. Plazomicin showed potent in vitro activity against multidrug-resistant Klebsiella pneumoniae and Escherichia coli.

Upstream product

• 1154758-62-9 tert-butyl ((2R,3R,4R,5R)-2-(((1S,2S,3R,4S,6R)-4-((tert-butoxycarbonyl)amino)-6-((S)-4-((tert-butoxycarbonyl)amino)-2-hydroxybutanamido)-3-(((2S,3R)-3-((tert-butoxycarbonyl)amino)-6-(((((4-nitrobenzyl)oxy)carbonyl)amino)methyl)-3,4-dihydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-4-yl)(methyl)carbamate 
• 1154758-59-4 6'-PNZ-2',3,3''-triBoc-sisomicin 
• 1154758-58-3 6'-PNZ-2',3,3''-triBoc-1-Fmoc-sisomicin 
• 1154758-55-0 4-nitrobenzyl (((2S,3R)-2-(((1R,2R,3S,4R,6S)-4-amino-6-((tert-butoxycarbonyl)amino)-3-(((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-3-((tert-butoxycarbonyl)amino)-3,4-dihydro-2H-pyran-6-yl)methyl)carbamate 
• 1154758-54-9 4-nitrobenzyl (((2S,3R)-3-amino-2-(((1R,2S,3S,4R,6S)-4,6-diamino-3-(((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-3,4-dihydro-2H-pyran-6-yl)methyl)carbamate 
• 32385-11-8 sisomicin 
• 1154758-63-0 tert-butyl ((2R,3R,4R,5R)-2-(((1S,2S,3R,4S,6R)-3-(((2S,3R)-6-(aminomethyl)-3-((tert-butoxycarbonyl)amino)-3,4-dihydro-2H-pyran-2-yl)oxy)-4-((tert-butoxycarbonyl)amino)-6-((S)-4-((tert-butoxycarbonyl)amino)-2-hydroxybutanamido)-2-hydroxycyclohexyl)oxy)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-4-yl)(methyl)carbamate 
• 1154758-74-3 6'-tert-butyldimethylsiloxyethyl-2',3,3-tri-(tert-butoxycarbonyl)-1-[N-tert-butoxycarbonyl-4-amino-2(S )-hydroxybutyryl]sisomicin 

Relevant articles and documents

Preparation method of Plazomicin

The invention provides a preparation method of Plazomicin. According to the method, a phosphoric acid solution is used for removing -Boc protecting groups in a precursor of Plazomicin, the reaction conditions are mild, and Plazomicin free base solid can be prepared after simple post-treatment is performed; and the prepared Plazomicin has a purity of 95% or above, and needs of industrial productioncan be met.

Synthetic method of plazomicin

The invention discloses a synthetic method of plazomicin. The method comprises the following steps: after dissociating sisomicin sulfate into sisomicin, all amino groups and hydroxyl groups of the sisomicin are protected by adopting TMS; 1-[N-tert-butyloxycarbonyl-4-amino-2(S)- hydroxybutyryl]-cisomicin is obtained by means of selective condensation of a 1-amino group and N-tert-butyloxycarbonyl-4-amino-2(S)-hydroxybutyric acid, then 6'-amino group is protected by using Cbz, other amino groups are protected by using Boc, through removing Cbz by hydrogenation, reductive amination is carried out, and a protecting group is removed under an acidic condition to obtain plazomicin. Compared with the existing synthesis method, the method has the advantages of short synthesis route, simple operation steps, mild reaction conditions, simple post-treatment and high product yield, and is more suitable for industrial mass production.

TREATMENT OF URINARY TRACT INFECTIONS WITH ANTIBACTERIAL AMINOGLYCOSIDE COMPOUNDS

A method for treating a urinary tract infection in a mammal in need thereof is disclosed, the method comprising administering to the mammal an effective amount of an antibacterial aminoglycoside compound.