SYNTHESIS OF 3,4-ANHYDRO-1-DEOXY-3-C-METHYL-D-HEXULOSE DERIVATIVES

Article abstract of DOI:10.1016/S0008-6215(00)90023-5

Epoxidation of (E)-1,3,4-trideoxy-5,6-O-isopropylidene-3-C-methyl-D-glycero-hex-3-enulose by alkaline hydrogen peroxide gave a mixture of 3,4-anhydro-1-deoxy-5,6-O-isopropylidene-3-C-methyl-D-arabino- (2) and -D-xylo-hexulose (3) that was resolved by chromatography.From the reaction of 2 with 3-chloroperbenzoic acid, the Baeyer-Villiger rearrangement product (2R)-2-O-acetyl-2,3-anhydro-1-deoxy-4,5-O-isopropylidene-D-erythro-pentulose hydrate was isolated.The structures and configurations of the above products were established on the basis of chemical transformations and analytical and spectroscopic data.