Glycomimetics via a new glycoexoenitols–malonyl radical C–C bond formation

Abstract

C-Glycosyl methylenemalonates 2 and 4, useful precursors for the synthesis of glycopeptides and glycoproteins mimics, are obtained by reaction of a malonyl radical on the glycoexoenitols 1 and 3; reaction of the same radical with 6-deoxy-1,2:3,4-di-O-isopropylidene-β-L-arabino- hex-5-enopyranose 5 results in a mixture of the malonylderivatives 6, 7 and 8 and, in diluted THF solutions, also in the tetrahydrofuranyl derivative 9.