28817-88-1

Basic information

• Product Name: methyl α-D-glucopyranuronate
• Synonyms: methyl α-D-glucopyranuronate
• CAS NO: 28817-88-1
• Molecular Weight: 208.168
• Mol File: 28817-88-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl α-D-glucopyranuronate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl α-D-glucopyranuronate(28817-88-1)
• EPA Substance Registry System: methyl α-D-glucopyranuronate(28817-88-1)

Safety Data

• Hazardous Substances Data: 28817-88-1(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 643-33-4 D-galacturonic acid 
• 25253-46-7 (3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carboxylic acid 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 489-91-8 D-galacturonic acid 
• 18524-41-9 (3aR,5S,5aR,8aS,8bR)-methyl-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-carboxylate 
• 685-73-4 D-galacturonic acid 

Downstream Products

• 905561-09-3 methyl 1,2,3,4-tetra-O-(3-fluorobenzoyl)-α-D-glucuronate 
• 905561-01-5 methyl 1-bromo-2,3,4-tetra-O-(3-fluorobenzoyl)-α-D-glucuronate 
• 905561-03-7 (2S,3S,4S,5R,6R)-3,4,5-Tris-(3-fluoro-benzoyloxy)-6-[(Z)-2-hydroxy-1-(7-methoxycarbonyl-heptyl)-dec-4-enyloxy]-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 6919-98-8 (2S,3R,4S,5R)-3,4,5-Triacetoxy-6-bromo-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 489-91-8 D-galacturonic acid 

Relevant articles and documents

A New Synthesis of D-Glycosiduronates from Unprotected D-Uronic Acids

O-Glycosidation of totally O-unprotected D-galacturonic acid 1 in THF provides α-pyranosides 4a when promoted with BF3*OEt2 whereas β-furanosides 6β were obtained in the presence of FeCl3; when the same reaction is performed with D-glucuronic acid 2 or 'D-glucurone' 3, alkyl-D-glucofuranosidurono-6,3-lactones 7 are synthesized in excellent yields and high β-selectivity.

The preparation and susceptibility to hydrolysis of novel O-galacturonoyl derivatives of carbohydrates

D-Galacturonic acid or (1->4)-α-D-galacturonan reacted in aqueous pyridine in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide with alcohols to yield esters.The alcohols that gave high yields of D-galacturonoyl derivatives were primary and included methanol, ethanol, 1-propanol, D-glucose, D-galactose, methyl β-D-glucopyranoside, methyl β-D-galactopyranoside, and cellulose.D-Galacturonic acid itself readily gave an O-D-galacturonoyl-D-galacturonic acid.The proposed structure of one compound, methyl 6-O-D-galacturonoyl-β-D-glucopyranoside, was supported by 1H and 13C NMR data and the FAB mass-spectral data.Each ester was hydrolysed at pH 11 and 25 deg C within 1 h.O-D-Galacturonoyl-D-glucose was considerably more alkali labile than O-polygalacturonoyl-D-glucose, and O-D-galacturonoylcellulose had an intermediate stability.The esters were relatively stable to cold acid, but could be hydrolysed by M trifluoroacetic acid at 100 deg C for 1 h.The esters tested were resistant to digestion by "Driselase", although the glycosidic bonds of O-polygalacturonoyl D-glucose were hydrolysed to yield O-oligogalacturonoyl-D-glucoses of low molecular weight.The possible application of these analytical methods to the detection of O-uronoyl-type cross-links in cell-wall polysaccharides is discussed.