L-Fuculose 1-Phosphate Barium Salt → L-Fuculose

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Crude L-fuculose-1-phosphate 4 (0.50 g) was powdered, dispersed in H2O (9 mL) and treated with Dowex 50W-X8 resin (H+ form, 400 mesh) until pH 2.8 for 30 min. The resin was filtered off, washed with water (2×2 mL) and the filtrate was adjusted to pH 4.7 with 6N HC1. Acid phosphatase (250 units) was added, the mixture was heated at 37° C. for 21 h, the pH was adjusted to 7.0 with saturated Ba(OH)2 soln. and methanol (2 vol) was added. The precipitate was filtered off through Celite and the solvent removed under reduced pressure. The residue was chromatographed on silica gel with CHCl3/Methanol (3:1). Compound 5 (123 mg, 46% from DHAP) was obtained as a slightly yellowish oil: [α]=0° (c 1, water), [α]D=0° (c 1.9, water)]. NMR (1H and 13C) data were in accordance with literature values reported in Liu, K. K.-C.; Xajimoto, T.; Chen, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280, A sample was taken and converted to the 2-nitrophenylhydrazone derivative: m. p. 158-160° C. (Lit. Green, M.; Cohen, S. S. J. Biol. Chem. 1956, 219, 557 which reports m.p. as 162-163° C.).

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