SYNTHESIS OFL-ARABINOSE-5-C14

Abstract

L-Arabinose-5-C14was synthesized by the following route: D-xylose → D-gulono-1,4-lactone-1-C14 → 2,3:5,6-di-O-isopropylidene-D-gulono-1,4-lactone-1-C14 → 2,3-O-isopropylidene-D-gulono-1,4-lactone-1-C14 → 3,4-O-isopropylidene-2,5-L-arabino-urono-lactone-5-C14 → methyl-α,β-L-arabinofuranosido-methyl uronate-5-C14 → methyl-α,β-L-arabinofuranoside-5-C14 → L-arabinopyranose-5-C14. The overall radiochemical yield of L-arabinose-5-C14was about 14% based on KC14N used in the first step. The structures of the isopropylidene derivatives of D-gulono-lactone have been clarified.