213906-15-1

Upstream product

• 71200-17-4 (4S,5R,6R)-6-Benzyloxy-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 
• 98-88-4 benzoyl chloride 
• 213906-18-4 (4S,5R,6R)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 
• 3080-47-5 methyl (benzyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 188003-24-9 (4S,5R,6R)-4,5-Diacetoxy-6-benzyloxy-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 

Downstream Products

• 219864-52-5 (2R,3R,4R,5R,6R)-4,5-Bis-benzoyloxy-6-benzyloxy-3-bromo-2-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 219864-61-6 (1S,3R,4R,5R,6S)-4,5-Bis-benzoyloxy-3-benzyloxy-2,7-dioxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester 
• 208389-99-5 methyl (benzyl 2,3-di-O-benzoyl-β-D-glucopyranoside)uronate 
• 219865-11-9 (2R,3S,4S,5R,6R)-4,5-Bis-benzoyloxy-6-benzyloxy-2-bromo-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Conformational study of synthetic Δ4-uronate monosaccharides and glycosaminoglycan-derived disaccharides

Sixteen Δ4-uronate monosaccharides were chemically synthesized. Their carboxy group was protected as a methyl or benzyl ester, the anomeric hydroxyl group as a benzyl glycoside and the 2 and 3 hydroxyl groups were protected with different substitution patterns as both ester and ether derivatives. Disaccharides containing Δ4-uronates were prepared from heparin using heparin lyases. Their carboxy group was unprotected or protected as a benzyl ester and the two hydroxyls in the uronate moiety were free, as O-sulfo derivatives or acylated. The conformation of these unsaturated uronate monosaccharide and disaccharide residues was studied using 1H NMR by examining interproton vic inal coupling constants. The Δ4-uronate residue adopted either the 2H1 or the 1H2 conformations. The equilibrium between these two conformers was shown to be controlled by substitution pattern.