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Synthesis of tritium labelled 7‐dehydrocholesterol 5β,6β‐oxide
Author(s) -
Michaud Dennis P.,
Nashed Nashaat T.,
Jerina Donald M.
Publication year - 1986
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.2580230404
Subject(s) - chemistry , tritium , epoxide , oxide , solvent , tritiated water , radiochemistry , combinatorial chemistry , organic chemistry , catalysis , physics , nuclear physics
We report the synthesis of tritiated 7‐dehydrocholesterol 5β,6β‐oxide in high specific activity. Oxidation of 7α‐bromo‐cholesterol 5β,6β‐oxide to the 3‐keto epoxide followed by borotritide reduction, in a special buffer‐organic solvent system to minimize undesired rearrangement, regenerated the 3β‐hydroxyl group. Base‐assisted elimination produced the title compound.