The synthesis of [5α, 6α‐^3^H]‐5α‐androst‐16‐en‐3‐one, starting with the catalytic tritiation of 3β‐acetoxy‐androst‐5‐en‐17‐one, is described. The so‐called “boar taint ketone” was obtained with high specific activity (21 Ci/mmol) and radiochemical purity better than 98 %.
A simple and efficient synthesis of [3α-3H]5α-androst-16-en-3β-ol
✍ Scribed by S. Ren; D. Hesk; P. McNamara; D. Koharski
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- French
- Weight
- 110 KB
- Volume
- 49
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
An efficient one step synthesis of [3__α__‐^3^H]5__α__‐androst‐16‐en‐3__β__‐ol by NaBT~4~ reduction of a ketone precursor is described. The specific activity of the product was 21.6 Ci/mmol with a radiochemical purity >99%. Synthesis of the precursor, 5__α__‐androst‐16‐en‐3‐one, from commercially available 5__α__‐androst‐16‐en‐3__α__‐ol is also presented. Copyright © 2006 John Wiley & Sons, Ltd.
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P r e v i o u s l y , we had s u c e s s f u l l y s y n t h e s i z e d [ 5a. 6a-HIandrost-16-en-3-one (3) from 3B-acetoxy-androst-5-en-17-0ne (1) i n f i v e s t e p s 121. After c a t a l y t i c hydrogenation of t h e 5-double bond of (1) w i t h T2 t h e corresponding 17-tosylhydrazone had to
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