321746-79-6

Upstream product

• 321746-78-5 2-hydroxyethyl (methyl 2,3,4-tri-O-pivaloyl-β-D-glucopyranosyluronate)-(1-> 3)-4,6-di-O-actyl-2-O-benzoyl-β-D-galactopyranoside 
• 201789-48-2 (2S,3S,4S,5R,6R)-6-((2R,3S,4S,5R,6R)-3-Acetoxy-2-acetoxymethyl-6-allyloxy-5-benzoyloxy-tetrahydro-pyran-4-yloxy)-3,4,5-tris-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of 3-O-sulfoglucuronyl lacto-N-neotetraose 2-aminoethyl glycoside and biotinylated neoglycoconjugates thereof

The 2-aminoethyl glycoside of pentasaccharide 3-O-sulfo-GlcA(β-1→3)Gal(β-1→4)GlcNAc(β-1→3) Gal(β-1→4)Glc(β (1) and its conjugates with biotin and biotinylated polyacrylic acid were synthesized as molecular probes to investigate the recognition of the HNK-1 epitope containing carbohydrates by proteins. Key steps in the first of two investigated schemes for the preparation of the target compound 1 were (a) assembling of the pentasaccharide backbone (compound 10) by glycosylation of selectively substituted allyl glycoside of the trisaccharide GlcNAc(β-1→3)Gal(β-1→4)Glc(β with glucuronyl-galactose glycosyl donor, (b) transformation of the allyl aglycon in 10 into 2-azidoethyl one (to give 11), (c) selective deprotection of the OH group at C-3 of the GlcA residue in 11 via saponification, intramolecular formation of 6,3-lacton (13) and its methanolysis, and (d) subsequent O-sulfation. The alternative scheme with the use of 2-azido-ethyl glycoside of the trisaccharide GlcNAc(β-1→3)Gal(β-1→4)Glc(β instead of the allyl glycoside 6 was less effective due to smaller yield at the step of pentasaccharide synthesis. Additionally to 1 the 2-aminoethyl glycosides of the oligosaccharides GlcA(β-1→3)Gal(β-1→4)GlcNAc(β-1→3)Gal(β -1→4)Glc(β, 3-O-sulfo-GlcA(β-1→3)Gal(β, and GlcA(β-1→3)Gal(β were also synthesized.