83023-73-8

Upstream product

• 18281-92-0 β-D-glucurono-6,3-lactone 
• 108-24-7 acetic anhydride 
• 14984-34-0 sodium D-glucuronate 
• 104-15-4 toluene-4-sulfonic acid 
• 6556-12-3 D-glucuronic acid 
• 24016-65-7 D-glucuronic acid sodium salt 
• 489-91-8 D-glucuronic acid 
• 474426-72-7 acetic 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic anhydride 

Downstream Products

• 374105-87-0 phenacyl 2,3,4-tri-O-acetyl-α-D-glucopyranuronate 
• 474426-99-8 2,3,4-tri-O-acetyl-1-chloro-1-deoxy-α-D-glucopyranuron-N-phenylamide 
• 1345853-98-6 N-(2-chloro-4-nitrophenyl)-1,2,3-tri-O-acetyl-Δ4,5-β-D-glucopyranuronamide 
• 1345854-00-3 N-(2-chloro-4-nitrophenyl)-1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronamide 
• 4310-12-7 1,2,3,4-tetra-O-acetyl-N-benzyl-β-D-glucopyranuronamide 
• 1345853-88-4 N-benzyl-1,2,3-tri-O-acetyl-Δ4,5-β-D-glucopyranuronamide 
• 1345853-94-2 N-(4-bromophenyl)-1,2,3-tri-O-acetyl-Δ4,5-β-D-glucopyranuronamide 
• 1345853-96-4 N-(4-bromophenyl)-1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronamide 
• 499-05-8 comanic acid 
• 95722-14-8 1,2,3-tri-O-acetyl-4-deoxy-β-L-threo-4-hexenopyranuronic acid 
• 165319-89-1 6,7-dideoxy-1,2:3,4-tetra-O-acetyl-7-phenylsulphonyl-7-(2'-thiopyridyl)-α-L-ido-heptopyranose 
• 10344-94-2 p-nitrophenyl-β-D-glucuronide 
• 34351-67-2 p-methoxybenzyl-2,3,4-tri-O-acetyl-beta-D-glucuronic acid methyl ester 
• 18472-49-6 methyl <4'-nitrophenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid>uronate 

Relevant academic research and scientific papers

ACYLATED ACTIVE AGENTS AND METHODS OF THEIR USE FOR THE TREATMENT OF AUTOIMMUNE DISORDERS

Disclosed herein are acylated active agents (e.g., acylated catechin polyphenols, acylated carotenoids, acylated mesalamines, acylated sugars, acylated shikimic acids, acylated ellagic acid, acylated ellagic acid analogue, and acylated hydroxybenzoic acids), active agent combinations (e.g., with a second agent that is a fatty acid) and methods of their use, e.g., for modulating an autoimmunity marker or for treating an autoimmune disorder.

Preparation method of substituted benzyl or substituted phenyl beta-D-hexuronic acid glucoside

The invention relates to the technical field of pharmaceutical and chemical industries, and discloses a preparation method of substituted benzyl or substituted phenyl beta-D-hexuronic acid glucoside.The preparation method comprises the steps of taking hexuronic acid as a raw material, and performing acetylation, selective acyl removal, methyl esterification, bromization, aethrization and alkalinealcoholysis to form substituted benzyl or substituted phenyl beta-hexuronic acid glucoside with a structural formula as follows as shown in the description, wherein n is equal to 0-1; and R is o-, m-or para-hydrogen, nitryl, methoxy or halogen. The method is mild in reaction condition, simple in step and suitable for large-scale preparation, and a reaction reagent is easy to obtain.

First conjugates of the diterpenoid isosteviol and glucuronic acid

Conjugates of the diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) and glucuronic acid containing two diterpenoid (ent-beyerane) skeletons joined by a 1,6-hexanedicarboxylate spacer and β-D-glucopyranuronoyl moieties were synthesized for the first time.

Sweet anion receptors: Recognition of chiral carboxylate anions by d-glucuronic-acid-decorated diindolylmethane

Anion receptors containing glucuronic acid were synthesized, and their anion binding ability studied. Chirality of anionic guests derived from mandelic acid and amino acids can be distinguished not only in terms of stability constants but also by signific

Synthesis of some novel D-glucuronic acid acetylated derivatives as potential anti-tumor agents

A structurally diverse series of Δ4,5-uronamide derivatives have been chemically synthesized starting from D-glucuronic acid itself by means of acetylation, activation, amide bond formation and base-catalyzed elimination protocols. Structure el

Synthesis and surface-active properties of uronic amide derivatives, surfactants from renewable organic raw materials

Short chemical syntheses were developed to produce a new set of surfactants from uronic acids derived from widely available raw materials. Three different strategies were used to synthesize uronic amide derivatives, the structures of which were totally characterized by spectrometric methods (IR, MS, 1H-RMN and 13C-RMN). The best one, using an acid chloride as the synthetic intermediate, furnished the expected amides as a mixture of anomers in 46-58% global yield. Surface-active properties (CMC, γcmc, Γmax, A min) of homologous series of uronic acid N-alkylamides from C8 to C18 were also assessed. In general, these sugar-based surfactants exhibited good surface-activities, and appeared as valuable nonionic surfactants compared to octylphenol 9-10 ethylene oxide condensate, the most well-known nonionic surfactant. Increasing the alkyl chain length influenced the CMC values for both glucuronic and galacturonic N-alkylamide derivatives. The galacturonic N-alkylamides decreased γcmc at slower values than their counterpart's glucuronic N-alkylamides.

Synthesis of thioesters from carboxylic acids via acyloxyphosphonium intermediates with benzyltriethylammonium tetrathiomolybdate as the sulfur transfer reagent

(Chemical Equation Presented) An efficient protocol is reported for the synthesis of thioesters from carboxylic acids with use of acyloxy phosphonium salts as intermediates and benzyltriethyl-ammonium tetrathiomolybdate as the sulfur transfer reagent.

Synthesis and structural analysis of the anilides of glucuronic acid and orientation of the groups on the carbohydrate scaffolding

The synthesis of anilides derived from glucuronic acid is described. Secondary anilides had a Z configuration in the solid state and showed intramolecular and intermolecular hydrogen bonding. However, on the basis of NMR and IR studies, there was generall

1,2,3,4-Tetra-O-acetyl-β-D-gluco-pyranuronic acid monohydrate at 120 K and anhydrous 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose at 292 K

The structure of the title acid as the monohydrate, C14H 18O11·H2O, displays hydrogen bonding which connects the molecules in layers parallel to (101). In the anhydrous glucopyranose, C14H20O10, only chain connectivity is attained but, due to disorder of the OH group, only partially and in two modes, one less favoured than the other. This provides incomplete connectivity between molecules in corrugated layers parallel to (010).

Design, Synthesis, and Evaluation of a Liposaccharide Drug Delivery Agent: Application to the Gastrointestinal Absorption of Gentamicin

The design, synthesis, and evaluation of a liposaccharide (11) for use as an agent to enhance the gastrointestinal absorption of charged, hydrophilic drugs with poor membrane permeability is reported. 11 was designed to possess both surfactant and ion-pairing properties and was conveniently synthesized from D-glucuronic acid (2) and N-Boc-lipoamino acid (5) precursors in eight steps in good yield. Isothermal titration microcalorimetry was used to determine the critical micelle concentration of 11 (in PBS) to be 2.09 ± 0.01 mM with an enthalpy of demicellization of 4.91 ± 0.11 kJ/mol. The ability of 11 to enhance the gastrointestinal absorption of the aminoglycoside antibiotic gentamicin (1), a hydrophilic polycation with negligible oral bioavailability, was assessed in vivo using rats. Rats dosed orally with a mixture of 11 (100 mg/kg) and 1 (60 mg/kg) had a statistically significant (P ≤ 0.034) increase in Cmax, AUC120, and percent absolute bioavailability (F) compared to control 1 (60 mg/kg) alone. The highest bioavailability (F = 9.1 ± 2.0%) was achieved by dosing with the mixture 11 (100 mg/kg) and 1 (15 mg/kg). This represents a 6-fold increase in bioavailability compared to the control (F = 1.4 ± 0.3%). These results suggest that the molar ratio of 1:11 may be critical in optimizing the delivery system, a finding ascribed in part to the ion-pairing properties of 11. The effect of 11 on the gastrointestinal mucosa was assessed using light microscopy to examine tissue samples from rats used in the pharmacokinetic study. No morphological changes were found in either the esophagi or duodena of the rats examined. One rat dosed with 11 (100 mg/kg) and 1 (60 mg/kg) exhibited slight gastric erosion, which could be attributed to 11.