Original scientific paper

The Synthesis of some B₆ Vitamin Halophosphates

S. Elshani ; Faculty of Pharmacy and Biochemistry, University of Zagreb, 41000 Zagreb, Croatia, Yugoslavia
Lj. Butula ; Faculty of Pharmacy and Biochemistry, University of Zagreb, 41000 Zagreb, Croatia, Yugoslavia
I. Butula ; Ruđer Bošković Institute, 41000 Zagreb, Croatia, Yugoslavia
D. Vikić-Topić ; Ruđer Bošković Institute, 41000 Zagreb, Croatia, Yugoslavia
A. Berton ; Department of Inorganic and Metallorganic Chemistry University of Padova, 35100 Padova, Italy
A. Iriarte ; School of Basic Life Sciences, University of Missouri - Kansas Kansas City, Missouri, 64110 USA

Abstract

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).

Keywords

Hrčak ID:

137310

URI

https://hrcak.srce.hr/137310

Publication date:

15.10.1991.

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