Abstract
d-Ribose (1) in N,N-dimethylformamide containing a trace of p-toluenesulfonic acid is acetonated under kinetic control by ethyl (or methyl) isopropenyl ether (2) to give mainly 3,4-O-isopropylidene-β-d-ribopyranose (3), together with lesser proportions of 2,3-O-isopropylidene-d-ribofuranose (4), its 5-(2-alkoxy-2-propyl) ether (5 or 5a), and 1,5:2,3-di-O-isopropylidene-β-d-ribofuranose (6). Similar treatment of d-arabinose (10) gives mostly 3,4-O-isopropylidene-β-d-arabinopyranose (11) together with a minor proportion of 1,2:3,4-di-O-isopropylidene-β-d-arabinopyranose (12). The strucutres of the monoacetals 3 and 11 were confirmed by an acetylation-deacetonation-acetylation sequence.
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