51231-31-3Relevant articles and documents
A concise synthesis of 25-Hydroxycholesterol from hyodesoxycholic Acid
Jin, Can,Wang, Yulei,Sun, Bin,Su, Weike
, p. 96 - 99 (2018/03/21)
A simple, efficient and economical method has been developed for the synthesis of 25-hydroxycholesterol in seven steps from hyodesoxycholic acid with an overall yield of 39%. The preparation of the 3β-tetrahydropyranyloxychol-5-en-24-al from 3β-tetrahydropyranyloxychol-5-en-24-oic acid methyl ester with di-isobutylaluminium hydride was achieved instead of using the conventional two-step reaction, thus avoiding the use of the toxic oxidant CrO3. The terminal product was obtained by hydroxybromination of desmosterol with N-bromosuccinimide/H2O, followed by reduction and deprotection of the halohydrins with LiAlH4. This simplified route gave an increased overall yield and used economical and environmentally benign reagents.
Synthesis of Cholesterol and Derivatives substituted in the Side chain
Kirk, David N.,Varley, Michael J.,Makin, Hugh L.J.,Trafford, David J.H.
, p. 2563 - 2567 (2007/10/02)
The carbanion derived from 24-phenylsulphonylchol-5-en-3β-ol 3-tetrahydropyranyl ether (6) reacted with acetone to give the 24-phenylsulphonyl-25-hydroxycholesterol 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. Cholesterol has been obtained via a selective reduction of the Δ24-unsaturation in desmosteryl benzoate with di-imide, or more efficiently by reducing 25-hydroxycholesteryl 3,25-diacetate w ith litium in ethylamine, without significant loss of label.The labelled 24,25-dihydroxycholesterols were also prepared from desmosteryl benzoate.
