SYNTHESIS OF 6-BIS(HYDROXYMETHYL)TETRAHYDROPYRAN-2-CARBALDEHYDE DERIVATIVES

Cycloaddition of 1,3-dibromo-2-oxyallyl cation to 2-(benzyloxymethyl)f uran provided a 8-oxabicyclo[3.2.1]hept-6-en-3-one derivative that was transformed into ibromo-2-benzyloxymethyl-2,6-bis(hydroxymethyl)-4- ( methoxymethyloxy)tetrahydropyran. Selective protection and oxidation p roduced a protected 6-bis(hydroxymethyl)tetrahydropyran-2-carbaldehyde that could be used to carry out cross-aldolisations, opening an appro ach to the synthesis of C-disaccharide analogues mimicking sialic acid glycosides.