115192-84-2

Upstream product

• 55728-75-1 1,3,2',6'-tetrakis(N-benzyloxycarbonyl)-5,6-O-cyclohexylideneneamine 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 933-40-4 cycloxexanone dimethyl ketal 
• 22854-75-7 N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine 

Downstream Products

• 115192-85-3 1,3,2',6'-tetra-N-(benzyloxycarbonyl)-3',4'-di-O-(o-methoxybenzoyl)neamine 
• 115192-86-4 3,2',6'-tri-N-(benzyloxycarbonyl)-1-N:6-O-carbonyl-3',4'-di-O-(o-methoxybenzoyl)neamine 

Relevant academic research and scientific papers

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.