Synthesis of 6-deoxy-L-idose and L-acovenose from 1,2 : 5,6-di-O-isopropylidene-alpha-D-glucofuranose

A practical route toward the synthesis of 6-deoxy-L-idose and L-acovenose f rom 1,2:5,6-di-O -isopropylidene-alpha -D-glucofuranose is described. Key s teps include the stereoselective hydrogenation of 6-deoxy-1,2:3,5-di-O-isop ropylidene-alpha -D-xylo-hex-5-enofuranose, regioselective protection of 6- deoxy-1,2-O-isopropylidene-beta -L-idofuranose at O-5, and epimerisation of 6-deoxy-5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-beta -L-idofurano se at C-3. (C) 2001 Elsevier Science Ltd. All rights reserved.