77016-10-5

Upstream product

• 70209-55-1 benzyl 2-acetamido-3,6-di-O-benzyl-4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-2-deoxy-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 58700-48-4 Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranosid 
• 14146-27-1 benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside 
• 55287-49-5 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 70209-54-0 Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(β-D-galactopyranosyl)-α-D-glucopyranosid 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 

Relevant academic research and scientific papers

Bausteine von Oligosacchariden, XX. Synthese der Oligosaccharid-Determinanten der Blutgruppensubstanzen der Type 2 des ABH-Systems. Diskussion der &α-Glycosid-Synthese

The antigenic determinants of type 2 of blood-group substances A and B (23 and 24) as well as blood-group substance H (17) were synthesized by selective glycosidation reactions combined with a series of blocking and deblocking steps.The possibilities and optimization of the α-glycoside synthesis are discussed.In hemagglutination inhibition tests the synthetic haptens A and B of type 2 and type 1 show a similar selective inhibitory effect.In case of hapten H, however, great differences can be observed.Here the type 2 exhibited a strong inhibition activity, whereas type 1 only showed an extremly low activity.This leads to the conclusion that in the determinants of the ABH-system on the surface of erythrocytes the chemical structure of type 2 is predominating.

SYNTHESIS OF THE TETRASACCHARIDE O-α-L-FUCOPYRANOSYL-(1->2)-3)>-O-β-D-GALACTOPYRANOSYL-(1->4)-2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSE, THE ANTIGENIC DETERMINANT OF HUMAN BLOOD-GROUP B (TYPE 2)

Treatment of benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-β-D-galactopyranosyl-α-D-glucopyranoside with benzaldehyde in the presence of zinc chloride, followed by regioselective benzoylation (N-benzoylimidazole in dichloromethane) provided crystalline benzyl 2-acetamido-4-O-(3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside.Condensation of this disaccharide with 2,3,4-tri-O-benzyl-1-O-(N-methylacetimidyl)-β-L-fucopyranose in nitromethane in the presence of p-toluenesulfonic acid and molecular sieves 4 Angstroem gave benzyl O-(2,3,4,-tri-O-benzyl-α-L-fucopyranosyl)-(1->2)-O-(3-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside.Debenzoylation, followed by condensation with 2,3,4,6-tetra-O-benzyl-1-O-(N-methylacetimidyl)-β-D-galactopyranose under the same conditions provided a tetrasaccharide derivative that was catalytically hydrogenolyzed into the title compound.