Application of a phase transfer reaction to the synthesis of L-fructose
1995
Gizaw, Y. | BeMiller, J.N.
L-Fructose was prepared in five steps from L-sorbose. 1,2-0-Isopropylidene-alpha-L-sorbopyranose, prepared from l, was selectively tosylated using phase transfer catalysis to give 1,2-0-isopropylidene-3-0-(p-tolylsulfonyl)-a-L-sorbopyranose. 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 1,2-0-isopropylidene-alpha-L-fructopyranose, which was deacetonated to yield L-fructose.
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