Acetalation of Sucrose by Acetal Exchange with Concomitant Fission of the Glycosidic Bond. Some New Acetals of D-Glucose and Methyl α-D Fructofuranoside

DOI: 10.1039/P19810003176

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 3176 - 3181 (1981)

Update date:2022-09-26

Topics:

Authors:

Cortes-Garcia, Raul

Hough, Leslie

Richardson, Anthony C.

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Article abstract of DOI:10.1039/P19810003176

Prolonged reaction of sucrose with 2,2-dimethoxypropane in NN-dimethylformamide in the presence of toluene-p-sulphonic acid (0.3percent w/v) afforded, after acetylation, methyl 4,6-di-O-acetyl-1,3-O-isopropylidene-α-D-fructofuranoside together with four acetals of D-glucose, namely, (1S)-1-methoxy-1,2:3,4:5,6-tri-O-isopropylidene-D-glucitol, 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, 3-O-acetyl-1,2:4,6-di-O-isopropylidene-α-D-glucopyranose, and 1,2,3-tri-O-acetyl-4,6-O-isopropylidene-α,β-D-glucopyranose.The mechanism of formation of these compounds is discussed.Several derivatives of methyl α- and β-D-fructofuranosides have been prepared from methyl 1,3-O-isopropylidene-α-D-fructofuranoside.