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- Title
A concise synthesis of 25-hydroxycholesterol from hyodesoxycholic acid.
- Authors
Can Jin; Yulei Wang; Bin Sun; Weike Su
- Abstract
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/H 2O, 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.
- Subjects
CHEMICAL synthesis; HYDROXYCHOLESTEROLS; METHYL formate; ALUMINUM hydride; HALOHYDRINS
- Publication
Journal of Chemical Research, 2018, Vol 42, Issue 2, p96
- ISSN
1747-5198
- Publication type
Article
- DOI
10.3184/174751918X15184426915885