Synthesis of β‐sitosterol‐3‐14C
- 1 April 1970
- journal article
- Published by Wiley in Journal of Labelled Compounds and Radiopharmaceuticals
- Vol. 6 (2) , 111-123
- https://doi.org/10.1002/jlcr.2590060202
Abstract
The synthesis of β‐sitosterol‐3‐14C, specific activity 5 mCi/mM, radiochemical purity ≥98 %, is described. Starting from stigmasterol, the complete synthesis consists of eleven reaction steps. It is based on methods described in the literature. For some of the steps, a considerable improvement in yield has been achieved. The actual labelling step is the condensation of 4‐oxa‐Δ5‐stigmasten‐3‐one with phenyl acetate‐14C in the presence of sodium hydride. β‐Sitosterol‐3‐14C has been obtained with a chemical yield of 23 %, based on 4‐oxa‐Δ5‐stigmasten‐3‐one. The radiochemical yield was 10.3 %. Chemical and radiochemical purities of β‐sitosterol‐3‐14C have been determined by means of thin‐layer chromatography, gas‐liquid chromatography and mass spectrometry.Keywords
This publication has 16 references indexed in Scilit:
- Synthetic steroids. Part II. The deconjugation of Δ4-3-oxo-steroids. An improved method for the preparation of 3β-hydroxyandrost-5-ene-11,17-dioneJournal of the Chemical Society C: Organic, 1967
- 3β-hydroxy-1,5-bisdehydro steroidsSteroids, 1966
- The Reduction of Cholestenone Enol Acetate by Sodium Borohydride1Journal of the American Chemical Society, 1951
- The Conversion of Δ4-Cholestene-3-one to Cholesterol1Journal of the American Chemical Society, 1951
- Labeling of Steroids in the 4-Position1Journal of the American Chemical Society, 1951
- Steroids Labeled with Isotopic Carbon: Cholestenone and Testosterone1Journal of the American Chemical Society, 1950
- 476. A conversion of cholest-4-en-3-one into cholesterolJournal of the Chemical Society, 1950
- 321. Reduction by dissolving metals. Part VII. The reactivity of mesomeric anions in relation to the reduction of benzene ringsJournal of the Chemical Society, 1950
- RADIOACTIVE CHOLESTENONE1Journal of the American Chemical Society, 1947
- 159. Studies in the sterol group. Part XLV. Investigation of the homogeneity of sitosterol by oxidation with the Oppenauer reagentJournal of the Chemical Society, 1943