The periodate oxidation of sucrose in aqueous N,N-dimethylformamide

Sucrose has been oxidized with sodium periodate in 0–50% aqueous N,N-dimethylformamide (DMF). In 50% aqueous DMF the reaction is selective for the glucose ring, yielding a dialdehyde. The increased selectivity is not due to conformational factors but is ascribed to the dissociation of water from cyc...

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Bibliographic Details
Published in:Carbohydrate research 1992-03, Vol.226 (2), p.253-260
Main Authors: de Wit, Dirk, van den Berg, Ronald, Johansson, L.Anders M., van Rantwijk, Fred, Maat, Leendert, Kieboom, Antonius P.G.
Format: Article
Language:English
Subjects:
Carbohydrate Sequence
Chemistry
Dimethylformamide - chemistry
Exact sciences and technology
Kinetics and mechanisms
Molecular Sequence Data
Organic chemistry
Oxidation-Reduction
Periodic Acid - chemistry
Reactivity and mechanisms
Solutions - chemistry
Sucrose - chemistry
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Summary:Sucrose has been oxidized with sodium periodate in 0–50% aqueous N,N-dimethylformamide (DMF). In 50% aqueous DMF the reaction is selective for the glucose ring, yielding a dialdehyde. The increased selectivity is not due to conformational factors but is ascribed to the dissociation of water from cyclic periodate ester species which makes the reaction via the acyclic ester on fructose unfavourable.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(92)84073-2