STEREOSPECIFIC SYNTHESIS OF METHYL D,L-HEX-2-ULOPYRANOSIDES FROM FURAN COMPOUNDS

Article abstract of DOI:10.1016/0040-4020(82)85036-9

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-psico- configuration.The steric course of reduction, hydroxylation and epoxidation reactions were examined.