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Acetonation of some pentoses with 2,2-dimethoxypropane-N,N-dimethylformamide-p-toluenesulfonic acid
Authors:Makoto Kiso  Akira Hasegawa
Institution:Department of Agricultural Chemistry, Gifu University, Kakamigahara, Gifu 504 Japan
Abstract:d-Xylose, d-arabinose, and d-ribose were each treated with 2,2-dimethoxypropane in N,N-dimethylformamide containing a trace of p-toluenesulfonic acid. d-Xylose gave 3,5-O-isopropylidene-d-xylofuranose, 1,2:3,5-di-O-isopropylidene-α-d-xylofuranose, 1,2-O-isopropylidene-α-d-xylopyranose, and two acyclic di-O-isopropylidene derivatives. d-Arabinose gave the known 3,4-O-isopropylidene-β-d-arabinopyranose and 1,2:3,4-di-O-isopropylidene-β-d-arabinopyranose. d-Ribose gave 2,3-O-isopropylidene-d-ribofuranose almost exclusively.
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