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Stereospecific Synthesis Of Methyl D,L-hex-2-ulopyranosides From Furan Compounds

O. Achmatowicz, M. H. Burzynska
Published 1982 · Chemistry

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Abstract 2-Benzyloxymethyl-5-hydroxymethylfuran was converted, according to the known method, into methyl 1-O-benzyl-3,4-dideoxy- d,l -hex-3-en-2-ulopyranos-5-ulose. Reduction of the latter and hydroxylation or epoxidation, followed by the oxirane ring opening, afforded the title compounds with α-sorbo-, β-fructo-, α-tagato- and α-pisco- configuration. The steric course of reduction, hydroxylation and epoxidation reactions were examined.
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