The chemistry of unprotected sucrose: the selectivity issue

Yves Queneau (1) , Juliette Fitremann (1) , Stéphane Trombotto (2)

1 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
2 IMP-LMPB - Ingénierie des Matériaux Polymères - Laboratoire des Matériaux Polymères et des Biomatériaux

Some basic principles of the chemistry of unprotected sucrose, the most abundant pure organic molecule produced, are described. The relationships between the structure of sucrose in solution and the selectivity of its chemical transformations are emphasized. Using a selection of examples, it is demonstrated that the simple primary alcohol vs secondary alcohol order of reactivity cannot serve as a general rule for describing the relative reactivity of sucrose’s eight hydroxyl groups. Depending on the reaction conditions (solvent, electrophilic reagent, catalysis...) the nucleophilic behaviour of sucrose changes, leading to compounds substituted at different positions. Some specific positions, OH-2, 1′ and 3′, close to anomeric carbon atoms and involved in intramolecular hydrogen bonds, play an as important role in this chemistry as the primary OH-6 and 6′, whereas enzymatic catalysis leads to OH-1′ substituted derivatives. The synthesis of amphiphilic derivatives, in which the carbohydrate moiety serves as the hydrophilic part, is notably described. The use of aqueous media for sucrose chemistry is also discussed, showing that even water-sensitive electrophilic substrates can be used

Domaines: Catalyse

Yves Queneau, Juliette Fitremann, Stéphane Trombotto. The chemistry of unprotected sucrose: the selectivity issue. Comptes Rendus. Chimie, 2004, 7, pp.177-188. ⟨10.1016/j.crci.2003.10.014⟩. ⟨hal-00015815⟩