The Synthesis of some B6 Vitamin HalophosphatesReport as inadecuate

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Croatica Chemica Acta, Vol.64 No.2 October 1991. -

A series of new halo-derivates of pyridoxine-3-O- or 5’-0-phosphates and pyridoxal-3-O- or 5’-0-phosphates have been synthesized. In the reaction of partially protected pyridoxine and pyridoxal 3-5 with phosphorusoxychlo- ride in the presence of triethylamine, the following dichlorophosphates were obtained: 3,4’-0-isopropylidenepyridoxine-5’-0-dichlorophosphate 6, 4,5’-0- isobutilidenepyridoxine-3-O-dichlorophosphate 7, and monoethylacetal-3-O- dicholorophosphate 8. Dichlorophosphates 6-8 reacted with NaF under catalytic action of 18-crown-6-ether, giving the corresponding difluorophos- phates 14-16. The 3,4’-0-isopropyiidene pyridoxine-5’-0-difluorophosphate 14, 4’,5’-isobutilydene-3-0-difluoro-phosphate 15 and monoethylacetal-3-O-di- fluorophosphate 16, in the reaction with aniline, yielded the corresponding monofluorophosphates in the form of aniline salts 17-19. The direct fluor- ination of pyridoxal-5’-phosphate with dinitrofluorobenzene yielded pyridox- al-5’-0-monofluorophosphate I which was isolated as cyclohexylamine salt 2.

Author: S. Elshani - ; Faculty of Pharmacy and Biochemistry, University of Zagreb, 41000 Zagreb, Croatia, Yugoslavia Lj. Butula - ; Facul



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