Convenient preparation of α- and β-glycosides of novel isomeric 3-deoxy-hept-2-ulosaric acids diesters

Article abstract of DOI:10.1016/S0040-4020(97)00675-3

Methyl 3-deoxy-α and β-D-ribo, D-xylo and D-lyxo-hept-2-ulosonic acids were obtained from the individual α and β anomers of the same methyl (methyl 3-deoxy-D-arabino-hept-2-ulopyranosid)onate in a sequential epimerisation at C-4 and/or C-5 of their appropriate O-trifluoromethanesulfonic derivatives, using cesium acetate. Subsequent oxidation of the 7-OH group in these compounds lead to the new isomeric 3-deoxy-hept-2-ulosaric acids derivatives.