144685-09-6

Basic information

• Product Name: 2,4-di-O-benzyl-3,6-dideoxy-α-L-xylo-hexopyranosyl bromide
• Synonyms: 2,4-di-O-benzyl-3,6-dideoxy-α-L-xylo-hexopyranosyl bromide
• CAS NO: 144685-09-6
• Molecular Weight: 391.305
• Mol File: 144685-09-6.mol

Chemical Properties

• CAS DataBase Reference: 2,4-di-O-benzyl-3,6-dideoxy-α-L-xylo-hexopyranosyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-di-O-benzyl-3,6-dideoxy-α-L-xylo-hexopyranosyl bromide(144685-09-6)
• EPA Substance Registry System: 2,4-di-O-benzyl-3,6-dideoxy-α-L-xylo-hexopyranosyl bromide(144685-09-6)

Safety Data

• Hazardous Substances Data: 144685-09-6(Hazardous Substances Data)

Upstream product

• 190248-99-8 ethyl 2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-L-xylo-hexopyranoside 
• 81413-19-6 methyl 2,4-di-O-benzyl-3,6-dideoxy-α-L-xylo-hexopyranoside 
• 85451-37-2 2,4-di-O-benzyl-3,6-dideoxy-L-xylo-hexopyranose 

Downstream Products

• 144685-21-2 methyl 2-acetamido-4-O-<3-O-benzoyl-4,6-O-benzylidene-2-O-(2,4-di-O-benzyl-3,6-dideoxy-α-L-xylo-hexopyranosyl)-β-D-galactopyranosyl>-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

Stereoselective Syntheses of the Conjugation-Ready, Downstream Disaccharide and Phosphorylated Upstream, Branched Trisaccharide Fragments of the O-PS of Vibrio cholerae O139

N-Bromosuccinimide-mediated 4,6-O-benzylidene ring opening in 8-azido-3,6-dioxaoctyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside afforded the corresponding 4-O-benzoyl-6-bromo-6-deoxy analogue, which was coupled with 3,4,6-tri-O-ace

Synthesis of a Conjugation-Ready, Phosphorylated, Tetrasaccharide Fragment of the O-PS of Vibrio cholerae O139

A new pathway to the tetrasaccharide α-Colp-(1→2)-4,6-P-β-d-Galp-(1→3)-[α-Colp-(1→4)]-β-d-GlcpNAc-1-(OCH2CH2)3NH2 has been developed. Glycosylation of 8-azido-3,6-dioxaoctyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-d-glucopyranoside with 3,4,6-tri-O-acetyl-2-O-bromoacetyl-α-d-galactopyranosyl bromide afforded the β-linked disaccharide. Debromoacetylation followed by reductive opening of the benzylidene acetal afforded the disaccharide diol acceptor. Halide-assisted glycosylation with 2,4-di-O-benzyl-α-colitosyl bromide gave the 1,2-cis-coupling product. Deacetylation followed by regioselective phosphorylation gave isomeric (R,S)-(P)-4II,6II-cyclic phosphates, which were globally deprotected by one-step catalytic (Pd/C) hydrogenation/hydrogenolysis. The target tetrasaccharide, obtained in high overall yield, is amenable for conjugation to proteins.

Total Synthesis of the Complete Protective Antigen of Vibrio cholerae O139

The first chemical synthesis of the complete protective O-antigen of a human-disease-causing pathogenic bacterium is described. The synthesis involved a protecting-group strategy that facilitated the regioselectivity of the key transformations, stereosele

Chemical Synthesis of the Galacturonic Acid Containing Pentasaccharide Antigen of the O-Specific Polysaccharide of Vibrio cholerae O139 and Its Five Fragments

Three pentasaccharides, two tetrasaccharides, and a trisaccharide fragment of the O-specific antigen of Vibrio cholerae O139 were synthesized by applying 1 + 1, 2 + 1, 3 + 1, and 4 + 1 coupling strategies. The most challenging tasks involved were the synt

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.

Molecular recognition XII. The binding of the H human blood group determinants and congeners by a lectin of Galactia tenuiflora

The H-type 2 human blood group-related trisaccharide (α-L-Fuc-(1c->2b)-β-D-Gal-(1b->4a)-β-D-GlcNAc-OMe (52)) is bound by the anti-H lectin of Galactia tenuiflora very differently than by the lectin I of Ulex europaeus.The reason why the Galactia lectin bi