SYNTHESIS OF SACCHARINIC ACID DERIVATIVES

Article abstract of DOI:10.1016/0008-6215(84)85302-1

Hydroxylation of ethyl cis-2,3-dideoxy-4,5-O-isopropylidene-2-C-methyl-DL-glycero-pent-2-enonate (1) with osmium tetraoxide gave ethyl 4,5-O-isopropylidene-β-DL-galactosaccharinate (ethyl 4,5-O-isopropylidene-2-C-methyl-DL-lyxonate, 3) and ethyl 4,5-O-isopropylidene-α-DL-glucosaccharinate (ethyl 4,5-O-isopropylidene-2-C-methyl-DL-ribonate, 4).Similarly, the trans-isomer of 1 yielded a mixture of ethyl 4,5-O-isopropylidene-α-DL-galactosaccharinate (ethyl 4,5-O-isopropylidene-2-C-methyl-DL-xylonate, 5) and ethyl 4,5-O-isopropylidene-β-DL-glucosaccharinate (ethyl 4,5-O-isopropylidene-2-C-arabinonate, 6).Compounds 3-6 were transformed into the corresponding 1,4-lactones.