172949-55-2

Upstream product

• 128716-41-6 4-methoxybenzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 82469-72-5 3,4,6-tri-O-benzoyl-2-(benzoyloximino)-2-deoxy-α-D-arabino-hexopyranosyl bromide 
• 172949-54-1 3,4,6-tri-O-benzoyl-2-(benzoyloxyimino)-2-deoxy-β-D-arabino-hexopyranosyl N,N-diethyldithiocarbamate 

Downstream Products

• 172949-59-6 4-methoxybenzyl 2,3-O-isopropylidene-4-O-(2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-mannopyranosyl)-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

Syntheses of three interglycosidic isomers of N-acetyl-β-D-mannosaminyl- L-rhamnoses associated with O-antigens of several gram-negative opportunistic pathogens

We achieved practical, highly stereoselective syntheses of three interglycosidic isomers of N-acetyl-β-D-mannosaminyl-L-rhamnoses, among which a β(1→4)-isomer corresponds to the repealing unit of the O-antigen of lipopolysaccharide (LPS) from the opportunistic pathogens Pseudomonas cepacia O5 and Pseudomonas aeruginosa X (Meitert). The other isomers are a β(1→2)- disaccharide, a constituent of LPS from Escherichia coli O1A, and an artificial β(1→3)-isomer. The disaccharides were obtained by simple three- step reaction sequences from 2-(benzoyloxyimino)-2-deoxyglycosyl halides (mannosamine progenitor). β-Selective glycosylations of appropriately protected L-rhamnosyl acceptors were performed. Subsequent reduction of the 2-acyloxyimino function to an amino group, N-acetylation, and removal of the protecting groups provided the target disaccharides. 13C-NMR and nuclear Overhauser effect spectra proved to be useful for structural determination of the positional isomers of the disaccharides.