Isosucrose. Definitive structural assignment by spectral correlation to α,β- and α,α-Sucrose octaacetate (cas 126-14-7)s

Add time:09/29/2019    Source:sciencedirect.com

Three nonreducing disaccharides containing D-glucosyl and D-fructosyl groups, namely, “isosucrose” octaacetate (3), sucrose octaacetate (4), and “α,α-sucrose” octaacetate (5), give qualitatively identical mass spectra and are, therefore, related as diastereoisomers. Spin-coupling values in the 300-MHz n.m.r. spectra of 3,4, and 5 establish that the D-glucopyranosyl group is present in the 4C1(D) conformation, and that the anomeric configuration of this group is α in 4 and 5, and β in 3. In the n.m.r. spectra, the H-4 atom of the D-fructofuranosyl group of 3 and 5 resonates 0.5 p.p.m. upfield of the corresponding signal of 4, from which it was deduced that both 3 and 5 are α-D-fructofuranosides.

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