688744-66-3

Basic information

• Product Name: 1,3,2',6'-tetraazido-3',4'-di-O-acetylneamine
• Synonyms: 1,3,2',6'-tetraazido-3',4'-di-O-acetylneamine
• CAS NO: 688744-66-3
• Molecular Weight: 510.426
• Mol File: 688744-66-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,3,2',6'-tetraazido-3',4'-di-O-acetylneamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2',6'-tetraazido-3',4'-di-O-acetylneamine(688744-66-3)
• EPA Substance Registry System: 1,3,2',6'-tetraazido-3',4'-di-O-acetylneamine(688744-66-3)

Safety Data

• Hazardous Substances Data: 688744-66-3(Hazardous Substances Data)

Upstream product

• 182554-04-7 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine 
• 474266-81-4 hexaazido-hepta-O-acetyl neomycin 
• 108-24-7 acetic anhydride 
• 671809-10-2 1,3,2′,6′-tetraazidoneamine 
• 468065-21-6 hexaazidoneomycin B 
• 119-04-0 neomycin B 
• 3947-65-7 neomycin A 
• 688744-65-2 1,3,2’,6’-tetrazido-5,6-O-cyclohexylidene neamine 
• 15446-43-2 neamine tetrahydrochloride 

Downstream Products

• 1383687-49-7 3',4'-di-O-acetyl-5-[[(propylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-50-0 3',4'-di-O-acetyl-6-[[( propylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-51-1 5-[[(propylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-52-2 6-[[(propylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-55-5 5-[[(3-azidopropylamino)carbonyl]oxy]-3',4'-di-O-acetyl-1,3,2',6'-tetraazidoneamine 
• 1383687-56-6 6-[[(3-azidopropylamino)carbonyl]oxy]-3',4'-di-O-acetyl-1,3,2',6'-tetraazidoneamine 
• 1383687-57-7 5-[[(3-azidopropylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 
• 1383687-58-8 6-[[(3-azidopropylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine 

Relevant articles and documents

Synthesis of glycosidic (β-1′′→6, 3′ and 4′) site isomers of neomycin B and their effect on RNA and DNA triplex stability

Glycosidic (β-1′′→6, 3′ and 4′) site isomers of neomycin B (i.e., neobiosamine (β-1′′→6, 3′ and 4′) neamines) have been synthesized in a straightforward manner. Peracetylated neomycin azide was used as a common starting material to obtain neobiosamine glycosyl donor and 6, 3′,4′-tri-O-acetyl neamine azide that after simple protecting group manipulation was converted to three different glycosyl acceptors (i.e., 5,6,4′-, 5,3′,4′- and 5,6,3′-tri-O-acetyl neamine azide). Glycosylation between the neobiosamine glycosyl donor and the neamine-derived acceptors gave the protected pseudo-tetrasaccharides, which were converted, via global deprotection (deacetylation and reduction of the azide groups), to the desired site isomers of neomycin. The effect of these aminoglycosides on the RNA and DNA triplex stability was studied by UV-melting profile analysis.

Application of glycodiversification: Expedient synthesis and antibacterial evaluation of a library of kanamycin B analogues

The expedient synthesis of a library of kanamycin B analogues is reported. The revealed SAR will guide future designs in developing kanamycin-type aminoglycoside antibiotics against drug-resistant bacteria.