Tetrahedron

Stereospecific synthesis of methyl D, L-hex-2-ulopyranosides from furan compounds

O Achmatowicz, MH Burzyńska

文献索引：Achmatowicz, Osman; Burzynska, Maria H. Tetrahedron, 1982 , vol. 38, # 23 p. 3507 - 3513

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被引用次数: 16

摘要

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.