86319-58-6

Upstream product

• 3554-91-4 Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 
• 115973-68-7 benzyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-galactopyranoside 
• 112289-51-7 benzyl 2-acetamido-2-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 206751-89-5 N-((3aR,4R,6S,7R,7aR)-6-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-acetamide 

Downstream Products

• 206751-90-8 Acetic acid (2R,3R,4R,5R,6S)-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yl ester 
• 1227930-59-7 benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-galactopyranoside 
• 1227930-60-0 benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->3)-[3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->4)]-6-O-benzyl-2-deoxy-2-acetamido-α-D-galactopyranoside 
• 206751-97-5 (2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 206752-02-5 (2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 206752-01-4 (2R,3S,4S,5R,6R)-6-((2R,3R,4R,5R,6S)-3-Acetoxy-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-4-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 206752-03-6 (2R,3S,4R,5R,6R)-6-((2S,3R,4R,5R,6R)-3-Acetylamino-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-4-yloxy)-4-benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid 

Relevant academic research and scientific papers

Synthetic N -Acetyl- d -glucosamine based fully branched tetrasaccharide, a mimetic of the endogenous ligand for CD69, activates CD69+ killer lymphocytes upon dimerization via a hydrophilic flexible linker

On the basis of the highly branched ovomucoid-type undecasaccharide that had been shown previously to be an endogenous ligand for CD69 leukocyte receptor, a systematic investigation of smaller oligosaccharide mimetics was performed based on linear and bra

Synthesis of O-(2-O-sulfo-α-L-idopyranosyluronic acid)-(1 → 3)-2- acetamido-2-deoxy-4-O-sulfo-D-galactopyranose trisodium salt, a disaccharide fragment of dermatan sulfate

Benzyl 2-acetamido-2-deoxy-α, and β-D-glucopyranoside were converted in high yield into the corresponding D-galacto analogues through a three- step procedure. These later were transformed in a straightforward manner into benzyl 2-acetamido-4-O-acetyl-6-O-benzyl-2-deoxy-α, and β-D- galactopyranoside, respectively, which served as acceptors in glycosylation reactions with variously activated derivatives of methyl 2-O-benzoyl-3,O- benzyl-4-O-chloro-acetyl-L-idopyranuronate. Condensation of the chloride derivative promoted by silver triflate led unexpectedly to the formation of the β-linked disaccharide, whereas the trichloroacetimidoyl derivative afforded the expected α-linked disaccharide in 63% yield. O- Dechloroacetylation of this later, followed by 4-methoxybenzylation at O-4 of the uronic acid moiety, saponification of the esters, O-sulfonation of the free hydroxyls, and catalytic hydrogenation provided the title disaccharide in high yield, as its sodium salt.

A PRACTICAL SYNTHESIS OF 2-ACETAMIDO-2-DEOXY-3,4-DI-O-β-D-GALACTOPYRANOSYL-D-GALACTOPYRANOSE

Two different sugar derivatives having free hydroxyl groups have been employed for synthesis of the title trisacharide.In one attempt, benzyl 2-acetamido-6-O-benzyl-2-deoxy-α-D-galactopyranoside (8) was treated with an excess of 2,3,4,6-tetra-O-acetyl-α-D