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Lu H, Drelich A, Omri M, et al. Catalytic Synthesis of a New Series of Alkyl Uronates and Evaluation of Their Physicochemical Properties. Molecules. 2016;21(10)doi: 10.3390/molecules21101301.
Lu, H., Drelich, A., Omri, M., Pezron, I., Wadouachi, A., & Pourceau, G. (2016). Catalytic Synthesis of a New Series of Alkyl Uronates and Evaluation of Their Physicochemical Properties. Molecules (Basel, Switzerland), 21(10), . https://doi.org/10.3390/molecules21101301
Lu, Huiling, et al. "Catalytic Synthesis of a New Series of Alkyl Uronates and Evaluation of Their Physicochemical Properties." Molecules (Basel, Switzerland) vol. 21,10 (2016). doi: https://doi.org/10.3390/molecules21101301
Lu H, Drelich A, Omri M, Pezron I, Wadouachi A, Pourceau G. Catalytic Synthesis of a New Series of Alkyl Uronates and Evaluation of Their Physicochemical Properties. Molecules. 2016 Sep 28;21(10). doi: 10.3390/molecules21101301. PMID: 27689983; PMCID: PMC6273592.
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Molecules. 2016 Sep 28;21(10). doi: 10.3390/molecules21101301.

Catalytic Synthesis of a New Series of Alkyl Uronates and Evaluation of Their Physicochemical Properties.

Molecules (Basel, Switzerland)

Huiling Lu, Audrey Drelich, Mehdi Omri, Isabelle Pezron, Anne Wadouachi, Gwladys Pourceau

Affiliations

  1. TIMR EA 4297 UTC/ESCOM, Sorbonne University, University of Technology of Compiègne, Rue Personne de Roberval, Compiègne CEDEX 60200, France. [email protected].
  2. TIMR EA 4297 UTC/ESCOM, Sorbonne University, University of Technology of Compiègne, Rue Personne de Roberval, Compiègne CEDEX 60200, France. [email protected].
  3. LG2A, UMR CNRS 7378-Chemistry Institute of Picardy FR CNRS 3085, University of Picardy Jules Verne, 33 rue Saint Leu, Amiens CEDEX 80039, France. [email protected].
  4. TIMR EA 4297 UTC/ESCOM, Sorbonne University, University of Technology of Compiègne, Rue Personne de Roberval, Compiègne CEDEX 60200, France. [email protected].
  5. LG2A, UMR CNRS 7378-Chemistry Institute of Picardy FR CNRS 3085, University of Picardy Jules Verne, 33 rue Saint Leu, Amiens CEDEX 80039, France. [email protected].
  6. LG2A, UMR CNRS 7378-Chemistry Institute of Picardy FR CNRS 3085, University of Picardy Jules Verne, 33 rue Saint Leu, Amiens CEDEX 80039, France. [email protected].

PMID: 27689983 PMCID: PMC6273592 DOI: 10.3390/molecules21101301

Abstract

Large quantities (>3 g) of a new series of alkyl uronates were synthesized in two steps from commercial methyl hexopyranosides. Firstly, several tens of grams of free methyl α-d-glucopyranoside were selectively and quantitatively oxidized into corresponding sodium uronate using 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (TEMPO)-catalyzed oxidation. Hydrophobic chains of different length were then introduced by acid-mediated esterification with fatty alcohols (ethyl to lauryl alcohol) leading to the desired alkyl glucuronates with moderate to good yields (49%-72%). The methodology was successfully applied to methyl α-d-mannopyranoside and methyl β-d-galactopyranoside. Physicochemical properties, such as critical micelle concentration (CMC), equilibrium surface tension at CMC (γ

Keywords: TEMPO mediated oxidation; carbohydrate-based surfactants; sugar esters; uronic acids derivatives

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