Synthesis of [26,27-2H6] cholesterol and derivatives substituted in the side chain
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 2563-2567
- https://doi.org/10.1039/p19830002563
Abstract
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 with lithium in ethylamine, without significant loss of label. The labelled 24,25-dihydroxycholesterols were also prepared from [26,27-2H6]desmosteryl benzoate.This publication has 0 references indexed in Scilit: