Isopropylidenation of L-arabinose N,N-dimethylhydrazone
1985 ◽
Vol 50
(9)
◽
pp. 1994-1999
◽
Direct isopropylidenation of L-arabinose N,N-dimethylhydrazone (I) was studied. Four major products whose structures were proven were produced in varying ratios depending upon the conditions. 2,2-Dimethoxypropane and sulfuric acid at 20 °C gave a 36% yield of 2,3:4,5-di-O-isopropylidene-L-arabinose N,N-dimethylhydrazone (II). Attempted aldol condensations directly on this hydrazone with paraformaldehyde were unsuccessful. This hydrazone was readily hydrolyzed to the corresponding protected aldehyde VI which underwent an aldol-Cannizzaro reaction to give the branched chain pentitol VII in high yield.