108852-23-9

Upstream product

• 3080-47-5 methyl (benzyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 100-51-6 benzyl alcohol 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 

Downstream Products

• 5285-02-9 Benzyl alcohol glucuronide 
• 149125-49-5 methyl (benzyl 2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate 
• 188003-23-8 (2S,3S,4S,5R,6R)-6-Benzyloxy-3,4,5-tris-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 188003-26-1 (4S,5R,6R)-4,5,6-Tris-benzyloxy-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl ester 
• 1033702-58-7 (2S,3S,4S,5R,6R)-6-{2-[2-(4-Chloro-phenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl]-acetoxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid 
• 1033702-58-7 Licofelone glucuronide 
• 149125-50-8 2,2,2-trichloroethyl (benzyl 2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate 
• 188003-32-9 (2R,3R,4R,5R,6R)-4,5,6-Tris-benzyloxy-3-bromo-2-hydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester 
• 188003-31-8 (2R,3R,4R,5R,6R)-6-Benzyloxy-3-bromo-4,5-bis-(2,2-dimethyl-propionyloxy)-2-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 188003-42-1 (2R,4R,5R,6R)-4,5,6-Tris-benzyloxy-3-oxo-tetrahydro-pyran-2-carboxylic acid benzyl ester 
• 188003-36-3 (1S,3R,4R,5R,6S)-3,4,5-Tris-benzyloxy-2,7-dioxa-bicyclo[4.1.0]heptane-1-carboxylic acid benzyl ester 
• 188003-41-0 (2R,4R,5R,6R)-6-Benzyloxy-4,5-bis-(2,2-dimethyl-propionyloxy)-3-oxo-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 188003-35-2 (1S,3R,4R,5R,6S)-3-Benzyloxy-4,5-bis-(2,2-dimethyl-propionyloxy)-2,7-dioxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester 
• 188003-25-0 (4S,5R,6R)-6-Benzyloxy-4,5-bis-(2,2-dimethyl-propionyloxy)-5,6-dihydro-4H-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.

Synthesis and biological identification of the acyl glucuronide of the antiinflammatory drug ML-3000

The synthesis and identification in biological samples of the 1-O-acyl glucuronide 6 of the antiinflammatory drug ML-3000 is described. Starting with D-glucuronic acid γ-lactone, 2,3,4-tris(tert.-butyldimethysilyl) glucuronic acid trichloroethylester 4 wa

Regio and stereoselective conversion of Δ4-uronic acids to L-ido- and D-glucopyranosiduronic acids

Synthesis of L-ido- and D-glucopyranosiduronic acids was performed starting from protected Δ4-uronic acids 3a-f. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives 6a-d, which were converted to the corresponding epoxides 7a-d in high yields. Direct reduction of these epoxides using borane-tetrahydrofuran complex afforded the D-glucopyranosiduronic acids 9b-d, while Lewis acid rearrangement through the C-4 keto intermediate 10b-d afforded the L-idopyranosiduronic acids 11b-d.

Synthesis of glucuronides of α,β-unsaturated carboxylic acids

A practical synthetic method for glucuronides of α,β-unsaturated carboxylic acids is described.An essential point of this method is the use of groups removable using non-reducing conditions for the protection of the glucuronic acid.