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Inhibitors of sterol synthesis. Synthesis of [2,4‐ 3 H]5α‐cholest‐8(14)‐ene‐3β,7α,15α‐triol and [2,4‐ 3 H]5α‐cholest‐8(14)‐en‐38‐ol‐15‐one
Author(s) -
Parish Edward J.,
Schroepfer George J.
Publication year - 1981
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580181006
Subject(s) - chemistry , triol , ene reaction , yield (engineering) , derivative (finance) , sterol , tritium , isoprene , hydrochloric acid , tetrahydrofuran , organic chemistry , medicinal chemistry , nuclear chemistry , diol , chromatography , radiochemistry , cholesterol , solvent , biochemistry , materials science , copolymer , economics , financial economics , metallurgy , polymer , physics , nuclear physics
Oxidation of 5α‐cholest‐8(14)‐ene‐3β,7α,15α‐triol with silver carbonate‐celite gave 5α‐cholest‐8(14)‐ene‐7α,15α‐diol‐3‐one in 88% yield. Treatment of the latter compound with tritiated water under basic conditions gave a labeled product which was reduced with lithium tri‐ tert ‐butoxyaluminum hydride in tetrahydrofuran to give [2,4–H]5α‐cholest‐8(14)‐ene‐3β,7α,15α‐triol which was obtained in high purity after medium pressure liquid chromatography in the form of its triacetate derivative. Treatment of the labeled triol with concentrated hydrochloric acid in 95% ethanol gave the desired [2,4‐ 3 H]5α‐cholest‐8(14)‐en‐3β‐ol‐15‐one.