Acetonation of L-pentoses and 6-deoxy-L-hexoses under kinetic control using heterogeneous acid catalysts

Abstract

The fibrous polymer-supported sulfonic acid catalyst Smopex-101 H+ proved to be an efficient catalyst for the preparation of O-isopropylidene derivatives from a series of rare sugars. Acetonation of the reducing sugars L-arabinose, L-ribose, L-xylose, L-fucose, and L-rhamnose in N,N-dimethylformamide by 2,2-dimethoxypropane or 2-methoxypropene led to the formation of the kinetically favored di-O- and/or mono-O-isopropylidene derivatives in 46-88% yields. The method consists of a simple experimental procedure which does not require predried solvents or reagents. The catalyst is easily recovered and can be regenerated making the procedure economically viable even for large-scale synthesis.