35785-35-4

Upstream product

• 107952-58-9 methyl uronate 
• 72692-06-9 methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 
• 67-56-1 methanol 
• 92420-89-8 methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate 
• 13242-55-2 2,3,4-tri-O-acetyllevoglucosan 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 709-50-2 methyl beta-D-glucopyranoside 
• 15910-11-9 1,4-diacetoxy 1,3-butadiene 
• 108-24-7 acetic anhydride 
• 77824-29-4 methyl (methyl 4-O-acetyl-2,3-dideoxy-α-DL-threo-hex-2-enopyranosid)uronate 
• 77824-29-4 methyl (methyl 4-O-acetyl-2,3-dideoxy-α-DL-erythro-hex-2-enopyranosid)uronate 
• 6294-16-2 D-galacturonic acid 
• 124492-91-7 methyl 2,3,4-tri-O-acetyl-6-O-p-anisyldiphenylmethyl-α-D-galactopyranoside 
• 85749-09-3 methyl 6-O-(4-methoxytrityl)-α-D-galactopyranoside 

Downstream Products

• 18486-38-9 methyl β-D-glucuronopyranoside methyl ester 

Relevant academic research and scientific papers

GAS CHROMATOGTAPHY OF THE METHYL ETHERS OF METHYL (METHYL-α-D-GALACTO- AND MANNOPYRANOSID)URONATES

Conditions are proposed for the gas-chromatographic separation of the methyl ethers of methyl (methyl α-D-galacto- and mannopyranosid)uronates in the form of their complete acetates on the stationary phases OV-17, GE-XE-60, and QF-1.

Synthesis and characterization of the hexenuronic acid model methyl 4-deoxy-β-l-threo-hex-4-enopyranosiduronic acid

A facile synthetic scheme for the preparation of methyl 4-deoxy-β-l-threo-hex-4-enopyranosiduronic acid utilizing the commercially available methyl α-d-galactopyranoside as starting material has been developed. The synthesis sequence comprises six high yielding reaction steps: TEMPO oxidation, acetylation, methanolysis of the lactone, acetylation, β-elimination, and final removal of the protecting groups. Only one column chromatographic purification is needed throughout the whole sequence. The overall yield is 60%. The final product has been characterized by NMR, Raman, UVRR, FTIR, and HRMS.

Efficient Synthesis of Muramic and Glucuronic Acid Glycodendrimers as Dengue Virus Antagonists

Carbohydrates are involved in many important pathological processes, such as bacterial and viral infections, by means of carbohydrate-protein interactions. Glycoconjugates with multiple carbohydrates are involved in multivalent interactions, thus increasing their binding strengths to proteins. In this work, we report the efficient synthesis of novel muramic and glucuronic acid glycodendrimers as potential Dengue virus antagonists. Aromatic scaffolds functionalized with a terminal ethynyl groups were coupled to muramic and glucuronic acid azides by click chemistry through optimized synthetic strategies to afford the desired glycodendrimers with high yields. Surface Plasmon Resonance studies have demonstrated that the compounds reported bind efficiently to the Dengue virus envelope protein. Molecular modelling studies were carried out to simulate and explain the binding observed. These studies confirm that efficient chemical synthesis of glycodendrimers can be brought about easily offering a versatile strategy to find new active compounds against Dengue virus.

Synthesis and Antitubercular, Antimicrobial, and Hemolytic Activity of Methyl D-Glucopyranuronate and Its Simplest Derivatives

Methyl glucuronate and some of its simplest derivatives have been synthesized, and their antitubercular, antimicrobial, and hemolytic activities have been studied. The simplest derivatives of glucuronic acid have been shown for the first time to exhibit a high antitubercular activity which is comparable with the activity of isoniazid.

The stereoselectivities of tributyltin hydride-mediated reductions of 5-bromo-d-glucuronides to l-iduronides are dependent on the anomeric substituent: Syntheses and DFT calculations

One of the shortest synthetic routes to l-iduronic acid derivatives is via free radical reduction of the C-5 bromide of the corresponding protected d-glucuronic acid derivative. The epimerization of such C-5 bromides to the l-ido derivatives via reaction with tributyltin hydride was investigated. It was found that the stereoselectivity of the reaction was dependent on the anomeric substituent. If the substituent was fluoride the l-ido product was obtained exclusively in 65-72% yield whereas the O-methyl or O-acetyl derivatives led to isomeric mixtures of both the l-ido and d-gluco products in different ratios depending on the reaction conditions. DFT calculations were performed to determine the stereoelectronic factors that favour formation of the l-ido isomer from the fluoride and suggest the selectivity is due to a transition state gauche effect and an Sn-F interaction.

Koenigs-Knorr reaction of fusel alcohols with methyl (1-bromo-2,3,4-tri-O- acetyl-α-d-glucopyranosid)uronate leading to the protected alkyl glucuronides - Crystal structures and high resolution 1H and 13C NMR data

Crystal structures and high resolution 1H and 13C NMR spectral data for methyl (alkyl 2,3,4-tri-O-acetyl-β-d-glucopyranosid) uronates (alkyl = methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, i-butyl, n-pentyl, 2-methyl-1-butyl and 3-methyl-1-butyl) are presented.

Glycoside cleavage by a new mechanism in unsaturated glucuronyl hydrolases

Unsaturated glucuronyl hydrolases (UGLs) from GH family 88 of the CAZy classification system cleave a terminal unsaturated sugar from the oligosaccharide products released by extracellular bacterial polysaccharide lyases. This pathway, which is involved in extracellular bacterial infection, has no equivalent in mammals. A novel mechanism for UGL has previously been proposed in which the enzyme catalyzes hydration of a vinyl ether group in the substrate, with subsequent rearrangements resulting in glycosidic bond cleavage. However, clear evidence for this mechanism has been lacking. In this study, analysis of the products of UGL-catalyzed reactions in water, deuterium oxide, and dilute methanol in water, in conjunction with the demonstration that UGL rapidly cleaves thioglycosides and glycosides of inverted anomeric configuration (substrates that are resistant to hydrolysis by classical glycosidases), provides strong support for this new mechanism. A hydration-initiated process is further supported by the observed UGL-catalyzed hydration of a C-glycoside substrate analogue. Finally, the observation of a small β-secondary kinetic isotope effect suggests a transition state with oxocarbenium ion character, in which the hydrogen at carbon 4 adopts an axial geometry. Taken together, these observations validate the novel vinyl ether hydration mechanism and are inconsistent with either inverting or retaining direct hydrolase mechanisms at carbon 1.

DMT-MM mediated functionalisation of the non-reducing end of glycosaminoglycans

Efficient functionalisation of the non-reducing end of uronic acid derivatives and glycosaminoglycan-derived disaccharides using peptide coupling has been achieved, mediated by the water-soluble agent DMT-MM. The Royal Society of Chemistry.

Efficient glycosydation and/or esterification of d-glucuronic acid and its 6,1-lactone under solvent-free microwave irradiation

2,3,4-Tri-O-acetyl-d-glucurono-6,1-lactone was obtained 'one-pot' from d-glucuronic acid. The lactone opening with different alcohols in the presence of a variety of catalysts was studied. All reactions were performed under microwave irradiation in solvent-free conditions.

CHROMIC ACID OXIDATION IN THE SYNTHESIS OF URONIC ACIDS. USE OF THE O-LEVULINOYL GROUP TO MINIMIZE ACYL MIGRATION

In the chromate oxidation of a partially acylated sugar derivative to form the corresponding uronic acid, acyl migration to the primary alcohol group is a frequent cause of interference.In contrast to more commonly employed ester substituents, the O-levulinoyl group is far less prone to migration during oxidations with Jones reagent (chromic-sulfuric acids).Examples described here include levulinoyl at O-5 of acyclic and furanose derivatives, and both eq and ax O-4 of pyranose derivatives.It is also shown that, because of the acidity of the Jones reagent, use of the O-levulinoyl group, in combination with a primary p-anisyldiphenylmethyl substituent, permits sequential rapid hydrolysis of the latter and oxidation of the newly exposed alcohol group, which favors high overall yields.In contrast to its immobility in these oxidation reactions, when the leulinoyl group is on O-2 of an aldosyl bromide, it participates in 1,2-orthoester formation as rapidly as O-acetyl.The 2,3,4,6-tetraacetate of either anomer of methyl D-glucopyranoside is oxidized to a uronic acid in moderate yield, by chromic acid in 5:1 acetic acid-water.