1323024-76-5

Basic information

• Product Name: 8-azido-3,6-dioxaoctyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• Synonyms: 8-azido-3,6-dioxaoctyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• CAS NO: 1323024-76-5
• Molecular Weight: 900.118
• Mol File: 1323024-76-5.mol

Chemical Properties

• CAS DataBase Reference: 8-azido-3,6-dioxaoctyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 8-azido-3,6-dioxaoctyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside(1323024-76-5)
• EPA Substance Registry System: 8-azido-3,6-dioxaoctyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside(1323024-76-5)

Safety Data

• Hazardous Substances Data: 1323024-76-5(Hazardous Substances Data)

Upstream product

• 86520-52-7 2-[2-(2-azidoethoxy)ethoxy]ethanol 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 169557-88-4 ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamido)-1-thio-β-D-glucopyranoside 
• 635684-80-9 ethyl 2-deoxy-2-N-trichloroacetamido-1-thio-β-D-glucopyranoside 
• 399035-92-8 ethyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside 

Downstream Products

• 1323024-78-7 8-azido-3,6-dioxaoctyl 6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 1323024-79-8 8-azido-3,6-dioxaoctyl 4-O-benzyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 1323024-80-1 8-azido-3,6-dioxaoctyl 4-O-benzyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 1323024-81-2 8-azido-3,6-dioxaoctyl 4-O-benzyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosyluronate)-β-D-glucopyranoside 
• 1323024-77-6 8-azido-3,6-dioxaoctyl 4-O-benzoyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 

Relevant articles and documents

Practical synthesis of building blocks for oligosaccharides containing the β-d-Galp-(1→3)-β-d-Glc p NAc motif

An efficient, new pathway for the synthesis of the title sequence has been developed. The sequence has been obtained as a glycosyl donor, β-d-Galp-(1→3)-β-d-GlcpNAc-1-SEt, or equipped with a linker (spacer) suitable for conjugation to other molecules, β-d-Galp-(1→3)- β-d-GlcpNAc-1-(OCH2CH2)3N3. Both disaccharides have been obtained in crystalline condition for the first time and fully characterized. The existing synthesis of the intermediate disaccharide glycosyl donor was improved by conducting the silver triflate mediated glycosylation under base-deficient conditions in the presence of 1,1,3,3-tetramethylurea and in the absence of molecular sieves. Georg Thieme Verlag Stuttgart · New York.

Synthesis of the conjugation ready, downstream disaccharide fragment of the O-PS of Vibrio cholerae O:139

The linker-equipped disaccharide, 8-amino-3,6-dioxaoctyl 2,6-dideoxy-2-acetamido-3-O-β-d-galactopyranosyluronate-β-d- glucopyranoside (10), was synthesized in eight steps from acetobromogalactose and ethyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-1-thio-β-d- glucopyranoside. The hydroxyl group present at C-4II in the last intermediate, 8-azido-3,6-dioxaoctyl 4-O-benzyl-6-bromo-2,6-dideoxy-2- trichloroacetamido-3-O-(benzyl 2,3-di-O-benzyl-β-d-galactopyranosyluronate) -β-d-glucopyranoside (9), is positioned to allow further build-up of the molecule and, eventually, construction of the complete hexasaccharide. Global deprotection (9→10) was done in one step by catalytic hydrogenolysis over palladium-on-charcoal.