2000 carbohydrates

carbohydratesU 0500

30 - 191Synthesis of Perfluoroalkylated Sugars Catalyzed by Rabbit MuscleAldolase (RAMA). — The synthesis of 6-C-polyfluoroalkyl-D-fructose(VIII) is presented, involving the aldolase-catalyzed condensation of a suitablepolyfluoroalkylated aldehyde derivative (VI) with dihydroxyacetone hydrogencyclic phosphate (VII) as a key step. The synthesis of the polyfluoroalkyl-substituted aldehyde suitable for reaction in aqueous solution is achieved startingfrom acrolein diethyl acetal (I). Alkylation with polyfluorobutyl iodide followedby base-mediated elimination of HI provides acetal (IV), which undergoesSharpless asymmetric dihydroxylation to give the properly substituted opticallyactive acetal (V). — (ZHU, WEI; LI, ZUYI; Perkin 1 (2000) 7, 1105-1108;Shanghai Inst. Org. Chem., Chin. Acad. Sci., Shanghai 200032, Peop. Rep.China; EN)

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