SYNTHESIS OF 4-SELENO-D-FRUCTOSE DERIVATIVES AND AN INVESTIGATION OF THEIR UTILITY AS PRECURSORS OF UNSATURATED HEXULOFURANOSIDES

Article abstract of DOI:10.1016/0008-6215(89)84023-6

4-Seleno-D-fructose derivatives were prepared by opening of the epoxide ring of methyl 2,3-anhydro-α- and β-D-tagatofuranosides with phenyl selenide ion.The resulting β-hydoxyselenide system or the corresponding methanesulfonate could not be induced to undergo elimination, thus providing the first examples of stable β-methylsulfonyloxyselenides.Oxidation of methyl 1,6-di-O-(tert-butyldimethylsilyl)-3-O-methylsulfonyl-4-Se-phenyl-4-seleno-α-D-fructofuranoside to the corresponding selenoxide, followed by thermally induced syn-elimination of benzeneselenenic acid, provides a convenient route to the novel unsaturated hexulofuranoside, methyl 1,6-di-O-(tert-butyldimethylsilyl)-4-deoxy-β-L-glycero-hex-4-enulofuranoside, which was readily converted into methyl 4-deoxy-α-D-threo-hexulofuranoside.