Transesterification of Sucrose in Organic Medium: Study of Acyl Group Migrations

Autor:	Valérie Molinier, Alain Bouchu, Krzysztof Wisniewski, Juliette Fitremann, Yves Queneau
Rok vydání:	2003
Předmět:	Acylation chemistry.chemical_compound Sucrose Chemistry Carbohydrate chemistry Organic Chemistry Regioselectivity Organic chemistry Moiety Transesterification Nuclear magnetic resonance spectroscopy Biochemistry Acyl group
Zdroj:	Journal of Carbohydrate Chemistry. 22:657-669
ISSN:	1532-2327 0732-8303
Popis:	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. †This paper is dedicated to Professor Gerard Descotes on the occasion of his 70th birthday, in acknowledgement of his accomplishments in the field of carbohydrate chemistry, and of his continuing efforts for developing the use of renewab...
Databáze:	OpenAIRE
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