123499-65-0Relevant articles and documents
Proteinase N-catalysed regioselective esterification of sucrose and other mono- and disaccharides
Potier, Pierre,Bouchu, Alain,Gagnaire, Juliette,Queneau, Yves
, p. 2409 - 2419 (2001)
Crude Proteinase N was used as catalyst for the synthesis of carbohydrate (in particular sucrose) esters by transesterification of activated esters in organic solvents. Polymerisable or amphiphilic sucrose esters (methacrylates and laurates) were obtained
Transesterification of Sucrose in Organic Medium: Study of Acyl Group Migrations
Molinier, Valerie,Wisniewski, Krzysztof,Bouchu, Alain,Fitremann, Juliette,Queneau, Yves
, p. 657 - 669 (2007/10/03)
The tendency of the acyl groups located on the glucose part of sucrose fatty acid esters to undergo intramolecular migrations in organic medium and the regioselectivity of some transesterifications of sucrose were investigated by HPLC, in situ NMR spectroscopy and preparative methods. Extensive acylation on secondary positions of the glucose moiety followed by migrations is general for base catalysed transesterification. The stability of 3- and 6-O-acyl derivatives, two isomers being thermodynamically favored compared to others, was studied in a series of conditions. It is shown that the presence of water catalyzes the migration of the ester at OH-3 towards OH-6 in organic basic medium, whereas the ester at OH-6 appears more stable under either acidic or basic conditions.