تفاعل #78820

معادلة التفاعل

L-fuculose 1-phosphate

L-Fuculose 1-Phosphate Barium Salt

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Compound 5

المردود 56.9%

L-Fuculose

المردود 56.9%

المذيبات

H2O

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONtreated with Dowex 50W-X8 resin (H+ form, 400 mesh) until pH 2.8 for 30 min
2. 2
   ترشيحThe resin was filtered off
3. 3
   غسيلwashed with water (2×2 mL)
4. 4
   workup.ADDITIONAcid phosphatase (250 units) was added
5. 5
   workup.ADDITIONand methanol (2 vol) was added
6. 6
   ترشيحThe precipitate was filtered off through Celite
7. 7
   أخرىthe solvent removed under reduced pressure
8. 8
   أخرىThe residue was chromatographed on silica gel with CHCl3/Methanol (3:1)

الإجراء التجريبي

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.).

المصدر