A SYNTHESIS OF 2-DEOXY-3-O-METHYL-1,4-ALDONOLACTONES

Article abstract of DOI:10.1016/S0040-4020(01)96089-2

A practical synthetic route to 2-deoxy-3-O-methyl-1,4-aldonolactones is achieved.Isopropylidene derivatives of aldehyde sugars 1, (free or in lactol form), reacted with methyl hydrogen malonate to give α,β-unsaturated esters 2.In the case of lactols, the R group in 2 is not identical to the R in 1 (epimerisation occurs).Base-catalysed addition of methanol to the esters 2 afforded the epimeric ethers 3, acid hydrolisis of which yielded the 2-deoxy-3-O-methyl-1,4-aldonolactones 4.Degradation of the sugar chain permitted the assignment of the absolute configuration on C-3.