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

Temperatur

37 °C

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.).

1. additiontreated with Dowex 50W-X8 resin (H+ form, 400 mesh) until pH 2.8 for 30 min
2. filtrationThe resin was filtered off
3. washwashed with water (2×2 mL)
4. additionAcid phosphatase (250 units) was added
5. additionand methanol (2 vol) was added
6. filtrationThe precipitate was filtered off through Celite
7. customthe solvent removed under reduced pressure
8. customThe residue was chromatographed on silica gel with CHCl3/Methanol (3:1)

ORD-Eintrag

ord-cb5f9b1ca50d4f8cb75bd244396e4bbc

Quelldatensatz

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06713287B1