79365-97-2

Upstream product

• 33639-77-9 perbenzyl fucosyl bromide 
• 79365-96-1 benzyl 3,3',4',6'-tetra-O-benzoyl-β-di-N-acetylchitobioside 
• 100-51-6 benzyl alcohol 
• 79365-95-0 benzyl 6-O-acetyl-3,3',4',6'-tetra-O-benzoyl-di-acetylchitobioside 
• 79365-92-7 1,6-di-O-acetyl-3,3',4',6'-tetra-O-benzoyl-α-di-N-acetylchitobiose 
• 79365-93-8 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl)-6-O-acetyl-3-O-benzoyl-2-deoxy-α-D-glucopyranosyl chloride 
• 79365-94-9 2-methyl-<6-O-acetyl-3-O-benzoyl-1,2-dideoxy-4-O-(2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-β-D-glucopyranosyl)-α-D-glucopyrano><2,1-d>-2-oxazoline 
• 79365-91-6 1,6-anhydro-3,3',4',6'-tetra-O-benzoyl-β-di-N-acetylchitobiose 
• 79365-90-5 1,6-anhydro-β-di-N-acetylchitobiose 
• 50604-74-5 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3-O-acetyl-1,6-anhydro-2-deoxy-β-D-glucopyranose 

Downstream Products

• 93-58-3 benzoic acid methyl ester 

Relevant academic research and scientific papers

SYNTHESIS OF 2-ACETAMIDO-4-O-(2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL)-2-DEOXY-6-O-(α-L-FUCOPYRANOSYL)-D-GLUCOPYRANOSE (6-O-α-L-FUCOPYRANOSYL-DI-N-ACETYLCHITOBIOSE)

Benzyl 3,3',4',6'-tetra-O-benzoyl-β-di-N-acetylchitobioside (8) was prepared in 5 steps from 3,3',4',6'-tetra-O-acetyl-1,6-anhydro-β-di-N-acetylchitobiose by the following series of reactions; de-O-acetylation, benzoylation, acetolysis of the 1,6-anhydro-β-ring, benzyl glycosidation via oxazoline, and selective de-O-acetylation.Reaction of 8 with 2,3,4-tri-O-benzyl-α-L-fucopyranosyl bromide by a bromide ion-catalyzed reaction afforded benzyl 3,3',4',6'-tetra-O-benzoyl-6-O-(2",3",4"-tri-O-benzyl-α-L-fucopyranosyl)-β-di-N-acetylchitobioside (10) in 83.4 percent yield.After removal of the protecting groups of 10,6-O-α-L-fucopyranosyl-di-N-acetyl chitobiose (11) was obtained as needles. (13)C-NMR spectra data for 11 are presented.Keywords: - synthesis; 6-O-α-L-fucopyranosyl-di-N-acetylchitobiose; 1,6-anhydro-di-N-acetylchitobiose derivative; oxazoline glycosidation method; benzyl di-N-acetyl-chitobioside derivative; bromide ion-catalyzed glycosidation; selective de-O-acetylation; (13)C-NMR