1154758-63-0

Basic information

• Product Name: 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
• Synonyms: 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
• CAS NO: 1154758-63-0
• Molecular Weight: 949.106
• Mol File: 1154758-63-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 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(CAS DataBase Reference)
• NIST Chemistry Reference: 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(1154758-63-0)
• EPA Substance Registry System: 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(1154758-63-0)

Safety Data

• Hazardous Substances Data: 1154758-63-0(Hazardous Substances Data)

Upstream product

• 207305-60-0 (S)-4-[(tert-butoxycarbonyl)amino]-2-hydroxybutanoic acid 
• 32385-11-8 sisomicin 
• 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 
• 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 
• 1154758-58-3 6'-PNZ-2',3,3''-triBoc-1-Fmoc-sisomicin 
• 1154758-59-4 6'-PNZ-2',3,3''-triBoc-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 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1154759-63-3 6'-nosyl-6'-(N-Boc-5-amino-pentyl)-2',3,3''-triBoc-1-(N-Boc-4-amino-2(S)-hydroxy-butyryl)-sisomicin 
• 1154759-64-4 6'-(N-Boc-5-amino-pentyl)-2',3,3''-triBoc-1-(N-Boc-4-amino-2(S)-hydroxy-butyryl)-sisomicin 
• 1154757-24-0 ACHN-490 
• 1154758-74-3 6'-tert-butyldimethylsiloxyethyl-2',3,3-tri-(tert-butoxycarbonyl)-1-[N-tert-butoxycarbonyl-4-amino-2(S )-hydroxybutyryl]sisomicin 
• 1154759-62-2 6'-nosyl-2',3,3''-triBoc-1-(N-Boc-4-amino-2(S)-hydroxy-butyryl)-sisomicin 

Relevant articles and documents

ANTIBACTERIAL AMINOGLYCOSIDE DERIVATIVES

Disclosed are a new class of antibacterial aminoglycoside derivatives, pharmaceutical compositions containing such compounds, and application thereof in the preparation of drugs for treating diseases related to bacterial infections. Specifically disclosed are a compound represented by formula (II), pharmaceutically acceptable salts thereof, and isomers thereof.

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.

SYNTHESIS OF ANTIBACTERIAL AMINOGLYCOSIDE ANALOGS

The present disclosure relates to novel methods for preparing antibacterial sisomicin-type aminoglycoside compounds, as well as to related intermediates, and crystal forms thereof, useful in such methods.