Journal of the Chemical Society. Perkin transactions I p. 2563 - 2567 (1983)
Update date:2022-08-04
Topics:
Kirk, David N.
Varley, Michael J.
Makin, Hugh L.J.
Trafford, David J.H.
The carbanion derived from 24-phenylsulphonylchol-5-en-3β-ol 3-tetrahydropyranyl ether (6) reacted with <2H6>acetone to give the 24-phenylsulphonyl-25-hydroxy<26,27-2H6>cholesterol derivative (7a), which was reduced by sodium amalgam to a separable mixture of the labelled 25-hydroxycholesterol and cholest-5,24-dien-3β-ol (desmosterol) derivatives. <26,27-2H6>Cholesterol has been obtained via a selective reduction of the Δ24-unsaturation in <26,27-2H6>desmosteryl benzoate with di-imide, or more efficiently by reducing 25-hydroxy<26,27-2H6>cholesteryl 3,25-diacetate w ith litium in ethylamine, without significant loss of label.The labelled 24,25-dihydroxycholesterols were also prepared from <26,27-2H6>desmosteryl benzoate.
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