18486-38-9

Upstream product

• 67-56-1 methanol 
• 709-50-2 methyl beta-D-glucopyranoside 
• 186581-53-3 diazomethane 
• 4356-84-7 methyl β-D-glucopyranosiduronic acid 
• 643-33-4 D-galacturonic acid 
• 92420-89-8 methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate 
• 72692-06-9 methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 77-76-9 2,2-dimethoxy-propane 
• 30902-96-6 methyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 6556-12-3 D-glucuronic acid 
• 96553-02-5 methyl (28-Hydroxy-23,28-dioxoolean-12-en-3β-yl β-D-Glucopyranoside)uronate 

Downstream Products

• 108866-91-7 uridine diphosphate <6-³H>glucose 
• 169557-85-1 methyl (methyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate 

Relevant academic research and scientific papers

The improved synthesis of β-D-Glucuronides using TEMPO and t-butyl hypochlorite

TEMPO/t-BuOCl is used to oxidise β-D-glucosides to β-D-glacuronides in high yield as a pivotal step in the preparation of labelled glucuronides from labelled glucose samples.

Synaptosides A and A1, triterpene glycosides from the sea cucumber Synapta maculata containing 3-O-methylglucuronic acid and their cytotoxic activity against tumor cells

Two novel triterpene holostane glycosides, synaptosides A (1) and A 1 (2), have been isolated from the Vietnamese sea cucumber Synapta maculata (Synaptida, Apodida). Their structures were elucidated by spectroscopic methods (NMR and MS) and chemical transformations. Glycosides 1 and 2 have rare branched pentasaccharide carbohydrate chains featuring a 3-O-methylglucuronic acid residue not previously reported in glycosides from sea cucumbers and a 6-O-sulfated glucose. Glycoside 2 has an oxo group at C-7 and a 8(9)-double bond. All these structural features are unknown in glycosides from sea cucumbers. Glycoside 1 has moderate cytotoxic activity (IC50 8.6 μg/mL) and glycoside 2 is inactive against HeLa tumor cells.

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.

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.

Electroorganic synthesis 66: Selective anodic oxidation of carbohydrates mediated by TEMPO

The carbohydrates 4-15 are anodically oxidized with 2,2,6,6- tetramethylpiperidin-1-oxyl (TEMPO) as mediator. Selective and complete reaction at the primary hydroxyl groups affords the corresponding carboxylic acids 16-32 in moderate to excellent yield. Methyl α-D-glucopyranoside is converted in 98% yield to the uronic acid 16. Cyclic voltammetry shows that the oxydation is base-catalyzed and the oxidation of the hydroxy group with TEMPO+ (2) is rate determining.

2-Deoxy-2-trichloroacetamido-D-glucopyranose derivatives in oligosaccharide synthesis: from hyalouronic acid to chondroitin 4-sulfate trisaccharides

Suitably protected derivatives of phenyl 2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside, 6, 15 and 16, a new class of glycosyl donors, were tested in the reaction with sugar acceptors of low reactivity (i.e., the methyl uronate 2).This methodolog

Selective oxidation of monosaccharide derivatives to uronic acids

Primary hydroxyl groups in partially protected monosaccharide derivatives were selectively oxidised to carboxylic acids using sodium hypochlorite in the presence of catalytic amounts of 2,2,6,6-tetramethyl-1-piperidinyl oxy, free radical (TEMPO). Acetal,

Study on the Mechanism of Diazomethane Degradation of the Sugar-Aglycone Linkage in Gypsogenin 3-O-Glycoside

The mechanism of the diazomethane degradation of the sugar-aglycone linkage of the gypsogenin 3-O-glycoside (1) was studied.Since there are three kinds of functional groups in 1 - the 4α-aldehyde group in the aglycone, the carboxy, and the 4'-hydroxy group in the glucuronic acid - which are presumed to contribute to the degradation reaction, the role of each functional group was examined using synthesized model compounds.As a result of the study, only the 4α-aldehyde group was shown to be essential.By taking the above evidence and the reaction of aldehyde with diazomethane into account, the degradation is thought to proceed through an epoxide intermediate as shown in Scheme 6.The reaction of gypsogenin with diazomethane was also examined.

METHANOLYSIS STUDIES OF CARBOHYDRATES, USING H.P.L.C.

An h.p.l.c. system that separates carbohydrates as their methyl glycosides has been used to study the products obtained on treatment of various carbohydrates with methanolic hydrogen chloride.Results are presented for the monosaccharide composition of several polysaccharides, lactone and ester formation during the treatment of D-glucuronic acid, and relative rates of glycosidation vs. esterification during the treatment of D-galacturonic acid.