55728-75-1

Basic information

• Product Name: 1,3,2',6'-tetrakis(N-benzyloxycarbonyl)-5,6-O-cyclohexylideneneamine
• Synonyms: 1,3,2',6'-tetrakis(N-benzyloxycarbonyl)-5,6-O-cyclohexylideneneamine
• CAS NO: 55728-75-1
• Molecular Weight: 939.029
• Mol File: 55728-75-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,3,2',6'-tetrakis(N-benzyloxycarbonyl)-5,6-O-cyclohexylideneneamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2',6'-tetrakis(N-benzyloxycarbonyl)-5,6-O-cyclohexylideneneamine(55728-75-1)
• EPA Substance Registry System: 1,3,2',6'-tetrakis(N-benzyloxycarbonyl)-5,6-O-cyclohexylideneneamine(55728-75-1)

Safety Data

• Hazardous Substances Data: 55728-75-1(Hazardous Substances Data)

Upstream product

• 933-40-4 cycloxexanone dimethyl ketal 
• 22854-75-7 N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine 
• 15446-43-2 neamine tetrahydrochloride 
• 501-53-1 benzyl chloroformate 
• 3947-65-7 neomycin A 
• 82472-80-8 C₅₆H₆₆N₄O₁₄ 

Downstream Products

• 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 
• 419573-42-5 3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxycarbonyl-1-N,6-O-carbonyl-5-O-triethylsilyl-3',4'-di-O-methoxymethylneamine 
• 419573-53-8 6-O-[2-N-[4-(benzyloxycarbonyl)butylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)neamine 
• 419573-48-1 6-O-[2-N-[2-(benzyloxycarbonyl)ethylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethylneamine 
• 419573-49-2 6-O-[2-N-[3-(benzyloxycarbonyl)propylamino]ethylamino]-3,2',6'-tris(N-benzyloxycarbonyl)-1-N-tert-butoxylcarbonyl-5,3',4'-tri-O-methoxymethylneamine 

Relevant articles and documents

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TOTAL SYNTHESIS OF NEOMYCIN B

Total synthesis of neomycin B, a pseudo-tetrasaccharide aminoglycoside antibiotic, has been achieved through two key glycosylation reactions.Coupling of 3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-L-idopyranosyl chloride with 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose under modified Koenigs-Knorr conditions gave 70percent of the desired β-L disaccharide (3) and corresponding to neobiosamine in structure.After deisopropylidenation of 3 and acetylation, 1,2-di-O-acetyl-3-O-(3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-β-L-idopyranosyl)-5-O-benzoyl-D-ribofuranose was coupled to HO-5 of 3,2',6'-tri-N-(benzyloxycarbonyl)-1-N:6-O-carbonyl-3',4'-di-O-(o-methoxybenzoyl)neamine, using trimethylsilyl trifluoromethanesulfonate, to give 60percent of the pseudo-tetrasaccharide 19 possessing the framework and masked functionality corresponding to neomycin B.Deblocking and reduction of the azido groups then gave neomycin B.