Catalytic Synthesis of a New Series of Alkyl Uronates and Evaluation of Their Physicochemical Properties.
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 (γcmc), solubility, and Krafft temperature were measured, and the effect of structural modifications on surface active properties and micelle formation was discussed.
TIMR EA 4297 UTC/ESCOM, Sorbonne University, University of Technology of Compiègne, Rue Personne de Roberval, Compiègne CEDEX 60200, France. huiling.lu@utc.fr.
Huiling
H
Lu
TIMR EA 4297 UTC/ESCOM, Sorbonne University, University of Technology of Compiègne, Rue Personne de Roberval, Compiègne CEDEX 60200, France. audrey.drelich@utc.fr.
Audrey
A
Drelich
LG2A, UMR CNRS 7378-Chemistry Institute of Picardy FR CNRS 3085, University of Picardy Jules Verne, 33 rue Saint Leu, Amiens CEDEX 80039, France. mehdi.omri@u-picardie.fr.
Mehdi
M
Omri
TIMR EA 4297 UTC/ESCOM, Sorbonne University, University of Technology of Compiègne, Rue Personne de Roberval, Compiègne CEDEX 60200, France. isabelle.pezron@utc.fr.
Isabelle
I
Pezron
LG2A, UMR CNRS 7378-Chemistry Institute of Picardy FR CNRS 3085, University of Picardy Jules Verne, 33 rue Saint Leu, Amiens CEDEX 80039, France. anne.wadouachi@u-picardie.fr.
Anne
A
Wadouachi
LG2A, UMR CNRS 7378-Chemistry Institute of Picardy FR CNRS 3085, University of Picardy Jules Verne, 33 rue Saint Leu, Amiens CEDEX 80039, France. gwladys.pourceau@u-picardie.fr.
Gwladys
G
Pourceau
TEMPO mediated oxidation; carbohydrate-based surfactants; sugar esters; uronic acids derivatives
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