SYNTHESIS OF SOME DERIVATIVES OF 3-C-METHYL-D-PSICOSE, 3-C-METHYL-D-FRUCTOSE, AND 6-DEOXY-3-C-METHYL-D-PSICOSE

Article abstract of DOI:10.1016/S0008-6215(00)85229-5

The synthesis of di-O-isopropylidene derivatives of 3-C-methyl-D-psicose (3) and 3-C-methyl-D-fructose by the reaction of 1,2:4,5-di-O-isopropylidene-β-D-erythro-hexo-2,3-diulo-2,6-pyranose (2) with methylmagnesium iodide and methyllithium is described.The reaction of 2 with diazomethane and reduction of the resulting epoxides gave the same branched-chain sugars.Isomerisation of 3 and its transformation into the 6-deoxy-5-iodo derivative 9, followed by catalytic hydrogenation and hydrolysis of the isopropylidene groups, gave 6-deoxy-3-C-methyl-D-psicose.