Acetic Anhydride → 1,2:5,6-Bis-O-(1-methylethylidene)-alpha-D-allofuranose

Participants

Reaction Steps

Sowa, W. and Thomas, G. H. S., (Can. J. of Chem., 1966, Vol. 44, 836-838) used the DMSO/acetic anhydride oxidation of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose in small scale (10 mmole) using a 20 fold excess of acetic anhydride. The ulose was then reduced providing 1,2:5,6-di-O-isopropylidene-α-D-allofuranose of poor quality, thus the product had to be column purified. Overall this procedure is not suitable for large-scale productions due to the large reagent consumption, two step procedure and the column purification step.

Provenance & Evidence