Alternative synthesis for the preparation of 16α-[(18) F]fluoroestradiol

Journal of Labelled Compounds & Radiopharmaceuticals
Hee Seup KilDae Yoon Chi

Abstract

We have developed a new precursor, 3,17β-O-bis(methoxymethyl)-16β-O-p-nitrobenzenesulfonylestriol (14c) of 16α-[(18) F]fluoroestradiol ([(18) F]FES). Although we could not selectively protect the C17 alcohol in the presence of the C16 alcohol, we were able to prepare and chromatographically isolate the desired C16 TBDMS, C17,C3-dimethoxymethyl (diMOM) protected estriol derivative and convert into the ultimate fluorination precursor. The MOM protective group proved to be more quickly removed than the cyclic sulfate group. The di-MOM protective precursor at the C3 and C17 alcohols instead of a cyclic sulfate group shortened hydrolysis time. We prepared three different sulfonate precursors at C16 alcohol. After checking their reactivity in the [(18) F]fluorination step and considering the stability of the precursors, we obtained the best results with nosylate precursor 14c.

References

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