58700-48-4

Upstream product

• 70209-54-0 Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(β-D-galactopyranosyl)-α-D-glucopyranosid 
• 108-24-7 acetic anhydride 
• 55287-49-5 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 100-39-0 benzyl bromide 
• 14146-27-1 benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 

Downstream Products

• 77356-41-3 benzyl 2-acetamido-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 77396-73-7 benzyl 2-acetamido-4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 70209-58-4 benzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1<*>2)-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 77016-11-6 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-α-D-glucopyranoside 
• 77016-10-5 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-α-D-glucopyranoside 
• 70209-56-2 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 
• 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 
• 70209-57-3 benzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1<*>2)-O-(3-O-benzoyl-4,6-O-benzylidene-3-O-benzoyl-β-D-galactopyranosyl)-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 76909-80-3 Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-α-D-glucopyranosid 
• 77396-76-0 benzyl 2-acetamido-4-O-(4,6-di-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 77396-75-9 benzyl 2-acetamido-4-O-(2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 77356-40-2 N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((4aR,6S,7R,8R,8aR)-7,8-dihydroxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-3-yl]-acetamide 
• 77396-74-8 N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-acetamide 
• 70209-54-0 Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(β-D-galactopyranosyl)-α-D-glucopyranosid 

Relevant academic research and scientific papers

LEWISSAEURE-KATALYSIERTE SYNTHESEN VON DI- UND TRI-SACCHARID-SEQUENZEN DER O- UND N-GLYCOPROTEINE, ANWENDUNG VON TRIMETHYLSILYLTRIFLUOROMETHANESULFONAT

In the presence of trimethylsilyltrifluoromethanesulfonate as Lewis acid catalyst, β-acetates reacted, as glycosyl donors and with neighboring-group participation, with secondary hydroxyl groups of saccharides having low reactivity to give β-glycosidicall

Blood-group Ii-Active Oligosaccharides. Synthesis of a Tetrasaccharide, a β-(1->3) Dimer of N-Acetyl-lactosamine

Condensation of benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (2) with 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide, followed by de-O-acetylation, acetonation, O-benzoylation, and acidic hydrolysis afforded the 3',4'-diol (5) derived from N-acetyl-lactosamine.This compound was selectively glycosylated at the 3'-position by the oxazoline (7) derived from lactosamine to give the protected tetrasaccharide (8) in 52percent yield.Removal of the protecting groups gave the free tetrasaccharide β-D-Galp-(1->4)-β-D-GlcpNAc-(1->3)-β-D-Galp-(1->4)-D-GlcpNAc (9), a β-(1->3) dimer of N-acetyl-lactosamine.This structure has been found in various glycolipids isolated from erythrocyte membranes and could be recognized by several anti-i antisera.

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 Blood-group Substances. Part 11. Synthesis of the Trisaccharide O-α-D-Galactopyranosyl-(1-->3)-O-β-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-D-glucopyranose

Reaction of 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide with benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside in 1,2-dichloroethane in the presence of mercuric bromide and molecular sieves (4 Angstroem) provided after O-deacetylation