256490-31-0Relevant articles and documents
Synthesis of a fluorinated analogue of anticancer active ether lipids
Burchardt,Takahashi,Takeuchi,Haufe
, p. 2078 - 2084 (2001)
The synthesis of racemic 2′-(trimethylammonium)ethyl-3-hexadecyloxy-2-fluoro-2-(methoxymethyl) -prop-1-yl-phosphate (6), a fluorinated analogue of an anticancer active ether lipid 5 was realized with 3% overall yield in a nine-step synthesis starting from 2-methylene-1,3-propanediol (7) using a bromofluorination as the key step. Both enantiomers of the precursor 8 of the ether lipid 6 were synthesized by lipase-catalyzed desymmetrization of the diacetate 17, either by hydrolysis (83% ee) or by lipase-catalyzed acetylation of the diol 22 (82% ee). The antitumor activity of 6 has been found in an in vivo model of the methylcholanthrene-induced fibrosarcoma of mice.
