.delta.-Dicarbonyl sugars. 5. A novel synthesis of a branched-chain cyclitol

Cantrell, Charles E.; Kiely, Donald E.; Abruscato, Gerald J.; Riordan, James M.

doi:10.1021/jo00442a026

Cited by 16 publications

(9 citation statements)

References 10 publications

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“…19 p-Vinylbenzylamine was obtained through the azidation of pvinylbenzyl chloride and the following reduction with lithium aluminum hydride. 20 p-Vinylbenzyl chloride was kindly supplied by Seimi Chemical Co. Ltd. (Chigasaki, Kanagawa, Japan).…”

Section: Experimental Materialsmentioning

confidence: 99%

The Synthesis of the Glycopolymers Containing Pendant D,L-Xylaric and L-Tartaric Moieties and Their Inhibition Behavior on the β-Glucuronidase Activity

Kawaguchi

Kaida

Okawa

et al. 2008

Polym J

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New styrene derivatives having D,L-xylaric and L-tartaric moieties, N-p-vinylbenzyl-D,L-xylaramic and N-p-vinylbenzyl-Ltartaramic acids (VB-D,L-XylarH 10 and VB-L-TartaH 11), were synthesized by the ring-opening reaction of 2,3,4-tri-Oacetyl-meso-xylaric anhydride and 2,3-di-O-acetyl-L-tartaric anhydride with p-vinylbenzylamine, respectively, and their subsequent hydrolysis under basic condition. The glycomonomers were copolymerized with acrylamide (AAm) to give novel polymers having xylaric and tartaric moieties in the pendants (P(VB-D,L-XylarH-co-AAm) 12 and P(VB-L-TartaH-co-AAm) 13) respectively. The inhibition abilities of the resulting glycopolymers on the -glucuronidase activity were found to be much higher than not only that of the corresponding saccharic acids but also that of the glycomonomers, especially at the lower concentration of saccharic unit by the spectrophotometry. However, the inhibition values were lower than those of the glycopolymers bearing D-glucaric pendant, P(VB-6-D-GlucaH-co-AAm) (5) and P(VB-1-D-GlucaH-co-AAm) (6), reported in our previous work. The Lineweaver-Burk plot suggested that the glycopolymer 13 and the corresponding monomer 11 inhibit the -glucuronidase activity noncompetitively, whereas the inhibition behavior of glycopolymer 12 and monomer 10 is more complicated, probably a mix-type of uncompetitive and noncompetitive ones. These are in contrast to the competitive inhibition in the presence of the glycopolymer 5 and its monomer 1.

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Section: Experimental Materialsmentioning

confidence: 99%

The Synthesis of the Glycopolymers Containing Pendant D,L-Xylaric and L-Tartaric Moieties and Their Inhibition Behavior on the β-Glucuronidase Activity

Kawaguchi

Kaida

Okawa

et al. 2008

Polym J

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“…dicarboxylic acids obtained by oxidation of both the formyl group and the primary alcohol. The oxidation of d ‐xylose ( 2 ) with 70 % aqueous nitric acid led to the known [8] xylaric acid ( 42 ), a meso compound, in good yield (Scheme 4). Although the efficient reaction of aldaric acids with 1,2‐diaminobenzene leading to bis‐benzimidazole derivatives was already described in the literature, [9] we chose to replace the highly toxic o ‐phenylendiamine with the harmless 1,2‐diamino‐4,5‐dimethylbenzene 43 .…”

Section: Resultsmentioning

confidence: 99%

“…The residue was eluted from a column of silica gel with cyclohexane-AcOEt (from 10 : 1 to 3 : 1) to give 46 (470 mg, 36 %) as a syrup. 8,31.8,30.2,29.8,29.7,29.5,29.4,29.3,29.2,27.1,26.0,22.3 (CH 2 ); 20.5 (CH 3 ); 20.2 (CH 3 ); 14.0 (CH 3 ). HRMS (ESI) m/z calcd for C 61 H 105 N 4 O 3 (M + H) + 941.8187, found 941.8176.…”

Section: -Hydroxymethyl-5-[(1's)-1'2'-isopropylidenoxy-ethyl]-1-pheny...mentioning

confidence: 99%

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Synthesis of Chiral Ionic Liquids from Natural Monosaccharides

et al. 2022

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“…However, the research and commercialization activities on xylose oxidation to xylaric acid are very limited. About half a century ago, xylose oxidation with nitric acid reported 44 % xylaric acid yield . Highly exothermic reaction conditions and NO x gas release are some drawbacks in the nitric‐acid‐mediated oxidation.…”

Section: Introductionmentioning

confidence: 99%

Aerobic Oxidation of Xylose to Xylaric Acid in Water over Pt Catalysts

Sadula

Saha

2018

ChemSusChem

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Energy-efficient catalytic conversion of biomass intermediates to functional chemicals can make bio-products viable. Herein, we report an efficient and low temperature aerobic oxidation of xylose to xylaric acid, a promising bio-based chemical for the production of glutaric acid, over commercial catalysts in water. Among several heterogeneous catalysts investigated, Pt/C exhibits the best activity. Systematic variation of reaction parameters in the pH range of 2.5 to 10 suggests that the reaction is fast at higher temperatures but high C-C scission of intermediate C -oxidized products to low carbon carboxylic acids undermines xylaric acid selectivity. The C-C cleavage is also high in basic solution. The oxidation at neutral pH and 60 °C achieves the highest xylaric acid yield (64 %). O pressure and Pt amount have significant influence on the reactivity. Decarboxylation of short chain carboxylic acids results in formation of CO , causing some carbon loss; however, such decarboxylation is slow in the presence of xylose. The catalyst retained comparable activity, in terms of product selectivity, after five cycles with no sign of Pt leaching.

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.delta.-Dicarbonyl sugars. 5. A novel synthesis of a branched-chain cyclitol

Cited by 16 publications

References 10 publications

The Synthesis of the Glycopolymers Containing Pendant D,L-Xylaric and L-Tartaric Moieties and Their Inhibition Behavior on the β-Glucuronidase Activity

The Synthesis of the Glycopolymers Containing Pendant D,L-Xylaric and L-Tartaric Moieties and Their Inhibition Behavior on the β-Glucuronidase Activity

Synthesis of Chiral Ionic Liquids from Natural Monosaccharides

Aerobic Oxidation of Xylose to Xylaric Acid in Water over Pt Catalysts

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