Application of a phase transfer reaction to the synthesis of L-fructose

Article abstract of DOI:10.1016/0008-6215(94)00255-E

L-Fructose was prepared in five steps from L-sorbose (1). 1,2-O-Isopropylidene-α-L-sorbopyranose (2), prepared from 1, was selectively tosylated using phase transfer catalysis to give 1,2-O-isopropylidene-3-O-(p-tolylsulfonyl)-α-L-sorbopyranose (3).Formation of a 3,4-anhydro ring, followed by its base-catalyzed opening to effect overall inversion of configuration at both C-3 and C-4 gave 1,2-O-isopropylidene-α-L-fructopyranose (5), which was deacetonated to yield L-fructose (6).Keywords: Phase transfer catalysis; Synthesis of L-fructose; Fructose, L-