22854-75-7

Basic information

• Product Name: N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine
• Synonyms: N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine
• CAS NO: 22854-75-7
• Molecular Weight: 858.899
• Mol File: 22854-75-7.mol

Chemical Properties

• CAS DataBase Reference: N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine(22854-75-7)
• EPA Substance Registry System: N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine(22854-75-7)

Safety Data

• Hazardous Substances Data: 22854-75-7(Hazardous Substances Data)

Upstream product

• 15446-43-2 neamine tetrahydrochloride 
• 501-53-1 benzyl chloroformate 
• 41547-94-8 4-O-(2,6-di-deoxy-α-D-2,6-di-amine-glucopyranosyl)-2-deoxy-streptamine hydrochloride 
• 119-04-0 neomycin B 
• 3947-65-7 neomycin A 

Downstream Products

• 66787-82-4 3,2'-di-N-benzyloxycarbonyl-1,6:6',4'-N,O-carbonyl-neamine 
• 55728-75-1 1,3,2',6'-tetrakis(N-benzyloxycarbonyl)-5,6-O-cyclohexylideneneamine 
• 82472-80-8 C₅₆H₆₆N₄O₁₄ 
• 419573-40-3 3,2',6'-tris(N-benzyloxycarbonyl)-1-N,6-O-carbonyl-3',4'-di-O-methoxymethylneamine 
• 419573-43-6 3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-1-N,6-O-carbonyl-3',4'-di-O-methoxymethylneamine 
• 419573-45-8 3,2',6'-tris(n-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethylneamine 
• 419573-44-7 3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-1-N,6-O-carbonyl-5,3',4'-tri-O-methoxymethylneamine 
• 419573-47-0 3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethyl-6-O-(2-oxoethyl)neamine 
• 419573-41-4 3,2',6'-tris(N-benzyloxycarbonyl)-1-N,6-O-carbonyl-5-O-triethylsilyl-3',4'-di-O-methoxymethylneamine 
• 419573-39-0 1,3,2',6'-tetrakis(N-benzyloxycarbonyl)-3',4'-di-O-methoxymethylneamine 
• 419573-46-9 6-O-allyl-3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethylneamine 
• 419573-51-6 6-O-[2-N-[2-(benzyloxycarbonyl)ethylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)neamine 
• 419573-52-7 6-O-[2-N-[3-(benzyloxycarbonyl)propylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)neamine 

Relevant articles and documents

Designed spiro-bicyclic analogues targeting the ribosomal decoding center

The bacterial ribosome represents the confirmed biological target for many known antibiotics that interfere with bacterial protein synthesis. Aminoglycosides represent a lead paradigm in RNA molecular recognition and constitute ideal starting points for t

Regioselective modification of amino groups in aminoglycosides based on cyclic carbamate formation

Conditions for regioselective introduction of cyclic carbamate into per-N-Cbz neamine and per-N-Cbz kanamycin A have been found. The position and number of cyclic carbamate formed in these two aminoglycosides was controllable. On the base of selective cyclic carbamate formation, regioselective modification on N-1, N-6′ or both amino groups in neamine, and on N-6′, N-3″ or both amino groups in kanamycin A was achieved by ring-opening reaction with amines. A new neamine dimer linked at the N-1 was also synthesized with this method.

Design of novel antibiotics that bind to the ribosomal acyltransfer site

The structure of neamine bound to the A site of the bacterial ribosomal RNA was used in the design of novel aminoglycosides. The design took into account stereo and electronic contributions to interactions between RNA and aminoglycosides, as well as a ran

Rapid combinatorial synthesis of aminoglycoside antibiotic mimetics: Use of a polyethylene glycol-linked amine and a neamine-derived aldehyde in multiple component condensation as a strategy for the discovery of new inhibitors of the HIV RNA Rev responsive element

A library of neomycin B mimetics has been prepared rapidly without chromatography using a neamine-derived aldehyde, tert-butyl isocyanide or isocyanoacetic acid methyl ester, a glycine-conjugated polyethylene glycol (PEG) methyl ether, and various Cbz-N-protected amino acids as substrates in a Ugi-type one-pot reaction. The product linked to PEG was isolated by precipitation in ether. A simultaneous base-catalyzed hydrolysis and de-O-acetylation followed by hydrogenation provided an easy access to a library of neomycin B mimetics, which were screened for binding to the Rev responsive element of HIV mRNA (RRE). Several products were found to be more active than neamine with the IC50 values in the micromolar range.