1154758-54-9

Basic information

• Product Name: 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
• Synonyms: 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
• CAS NO: 1154758-54-9
• Molecular Weight: 626.664
• Mol File: 1154758-54-9.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 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(CAS DataBase Reference)
• NIST Chemistry Reference: 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(1154758-54-9)
• EPA Substance Registry System: 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(1154758-54-9)

Safety Data

• Hazardous Substances Data: 1154758-54-9(Hazardous Substances Data)

Upstream product

• 32385-11-8 sisomicin 
• 86832-06-6 1-{[(p-nitrobenzyl)oxy]carbonyl}-1H-benzotriazole 
• 69888-89-7 2,5-dioxopyrrolidin-1-yl (4-nitrobenzyl) carbonate 
• 4457-32-3 4-nitrobenzyl chloroformate 
• 193269-82-8 (N-hydroxy-5-norbomene-2,3-dicarboxylimido)-4-nitrobenzyl carbonate 
• 1154758-31-2 N-(4-nitrobenzyl carbonate)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid imide 
• 53179-09-2 Sisomicin sulfate 

Downstream Products

• 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 
• 1154758-63-0 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 
• 1154757-24-0 ACHN-490 
• 1154758-61-8 2',3,3''-triBoc-1-(N-Boc-3-amino-2(S)-hydroxy-propionyl)-sisomicin 
• 1154759-28-0 6'-PNZ-2',3,3''-triBoc-1-(N-phthalimido-2-amino-ethylsulfonamide)-sisomicin 
• 1154758-58-3 6'-PNZ-2',3,3''-triBoc-1-Fmoc-sisomicin 
• 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 

Relevant articles and documents

Effects of the 1-N-(4-Amino-2 S-hydroxybutyryl) and 6′- N-(2-Hydroxyethyl) Substituents on Ribosomal Selectivity, Cochleotoxicity, and Antibacterial Activity in the Sisomicin Class of Aminoglycoside Antibiotics

Syntheses of the 6′-N-(2-hydroxyethyl) and 1-N-(4-amino-2S-hydroxybutyryl) derivatives of the 4,6-aminoglycoside sisomicin and that of the doubly modified 1-N-(4-amino-2S-hydroxybutyryl)-6′-N-(2-hydroxyethyl) derivative known as plazomicin are reported together with their antibacterial and antiribosomal activities and selectivities. The 6′-N-(2-hydroxyethyl) modification results in a moderate increase in prokaryotic/eukaryotic ribosomal selectivity, whereas the 1-N-(4-amino-2S-hydroxybutyryl) modification has the opposite effect. When combined in plazomicin, the effects of the two groups on ribosomal selectivity cancel each other out, leading to the prediction that plazomicin will exhibit ototoxicity comparable to those of the parent and the current clinical aminoglycoside antibiotics gentamicin and tobramycin, as borne out by ex vivo studies with mouse cochlear explants. The 6′-N-(2-hydroxyethyl) modification restores antibacterial activity in the presence of the AAC(6′) aminoglycoside-modifying enzymes, while the 1-N-(4-amino-2S-hydroxybutyryl) modification overcomes resistance to the AAC(2′) class but is still affected to some extent by the AAC(3) class. Neither modification is able to circumvent the ArmA ribosomal methyltransferase-induced aminoglycoside resistance. The use of phenyltriazenyl protection for the secondary amino group of sisomicin facilitates the synthesis of each derivative and their characterization through the provision of sharp NMR spectra for all intermediates.

Preparation method of Plazomicin

The invention discloses a preparation method of Plazomicin. The method uses sisomicin as a starting material, HONB-PNZ is used for protecting aminos at allyl positions, a reaction with hexamethyldisilazane is conducted to prepare a fully-protected silanid

Preparation method of pradimicin antibiotics

The invention provides a preparation method of pradimicin antibiotics, belonging to the field of pharmaceutical chemistry and pharmaceutical engineering. The preparation method comprises the followingsteps: freeing of sisomicin, protection of amino, selective introduction of protective groups, deprotection of amino, and the like. The preparation method is suitable for industrial production, thushaving good market prospects.