5-(.alpha.-D-glucopyranosyloxymethyl)-furan-2-carboxaldehyde

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536 41, 536 172, 536 179, 536 177, 536 178, 536 53, C07H 1500

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active

052180980

ABSTRACT:
5-(.alpha.-D-glucopyranosyloxymethyl)-furan-2-carboxaldehyde (GMF) is produced from isomaltulose by heating a solution of isomaltulose in a strongly polar aprotic solvent in the presence of an acidic ion-exchanger, either batchwise or by percolation of the solution through a column filled with the ion-exchanger. Novel derivatives of GMF of the formula (I) ##STR1## wherein R' is a hydrogen atom, an acyl group or an alkyl group and X represents --CH.sub.2 OH, --COOH, --C(H).dbd.NOH, --CN, --CH.sub.2 NHR" or --CH.dbd.CR"R'", where R" is a hydrogen atom, an acyl or aryl group or an alkyl group with up to 20 C atoms and R'" is a hydrogen atom, --NO.sub.2, --CN, --COOalkyl or acyl are described, and also their preparation and use for the preparation of surface-active compounds.

REFERENCES:
Van Dam, H. E. et al., "The Conversion of Fructose and Glucose in Acidic Media: Formation of Hydroxymethylfurfural", Starch/Starke 38 (1986) No. 3, pp. 95-101.
Whistler, R. L. et al., Methods in Carbohydrate Chemistry. N.Y., Academic Press, 1962 pp. 316-317.

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