900180-45-2

Upstream product

• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 106294-96-6 8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 900180-43-0 8-azido-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 900180-44-1 8-azido-3,6-dioxaoctyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-glucopyranoside 

Downstream Products

• 900180-47-4 8-azido-3,6-dioxaoctyl 2-acetamido-6-O-benzyl-3-O-(3-O-benzyl-β-D-galactopyranosyl-(R)-P-4,6-cyclic 2,2,2-trichloroethyl phosphate)-2-deoxy-β-D-glucopyranoside 
• 900180-52-1 8-azido-3,6-dioxaoctyl 2-acetamido-6-O-benzyl-3-O-(3-O-benzyl-β-D-galactopyranosyl-(S)-P-4,6-cyclic 2,2,2-trichloroethyl phosphate)-2-deoxy-β-D-glucopyranoside 
• 900180-46-3 8-azido-3,6-dioxaoctyl 3-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of phosphorylated, conjugation-ready di-, tri- and tetrasaccharide fragments of the O-specific polysaccharide of V. cholerae O139

The fragments described contain a galactose residue with cyclic 4,6-phosphate and are equipped with an amino-functionalized spacer, allowing further derivatization or direct conjugation to suitable carriers. The core Gal-(1→3)-GlcNAc disaccharide was obtained by condensation of 8-azido-3,6-dioxaoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D- glucopyranoside with 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide under Helferich conditions. Reductive opening of the benzylidene acetal, followed by deacetylation and selective benzylation gave 8-azido-3,6-dioxaoctyl 2-acetamido-6-O-benzyl-3-O-(3-O-benzyl-β-D-galactopyranosyl) -2-deoxyβ-D-glucopyranoside, which was regioselectively phosphorylated to give two isomeric 4,6-cyclic 2,2,2-trichloroethyl phosphates. The (R)-phosphate was subjected to catalytic hydrogenation/hydrogenolysis to give the fully deprotected title disaccharide fragment. Glycosylation of the (S)-phosphate diol with 2,4-di-O-benzyl-3,6-dideoxy-α-L-xylo-hexopyranosyl bromide under halide-assisted conditions yielded a mixture of the tetrasaccharide and a trisaccharide, which were readily separable by chromatography. Their hydrogenation/ hydrogenolysis effected global deprotection as well as reduction of the azide, to furnish the deprotected title tri- and tetrasaccharide. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Synthesis of spacer-equipped phosphorylated di-, tri- and tetrasaccharide fragments of the O-specific polysaccharide of Vibrio cholerae O139

The synthesis of oligosaccharide fragments of the O-specific polysaccharide of Vibrio cholerae O139 containing a 4,6-cyclic phosphate galactose residue linked to GlcNAc is described. 8-Azido-3,6-dioxaoctyl 2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl-(1→3)