A Concise Synthesis of 25-Hydroxycholesterol from Hyodesoxycholic Acid. (February 2018)

• Record Type: Journal Article
• Authors: Jin, Can; Wang, Yulei; Sun, Bin; Su, Weike
• Is Part Of: Journal of chemical research. Volume 42:Number 2(2018)
• Page Start: 96
• Page End: 99
• Publication Date: 2018-02
• Subjects: hyodesoxycholic acid -- di-isobutylaluminium hydride -- 3β-tetrahydropyranyloxychol-5-en-24-al -- hydroxybromination -- 25-hydroxycholesterol; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.3184/174751918X15184426915885
• Languages: English
• ISSNs: 1747-5198

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/H2 0, 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.