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The synthesis of cholesterol‐2,2,4,4,6‐d 5
Author(s) -
Gruenke Larry D.,
Craig J. Cymerman
Publication year - 1979
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.2580160316
Subject(s) - chemistry , sodium borohydride , ethanol , deuterium , solvent , enol , cholesterol , sodium , medicinal chemistry , tritium , nuclear chemistry , radiochemistry , organic chemistry , catalysis , biochemistry , quantum mechanics , nuclear physics , physics
Cholesterol‐3,4‐d 2 and ‐2,2,4,4,6‐d 5 have been synthesized from Δ 4 ‐ cholestene‐3‐one for use as mass spectrometric stable isotope internal standards. Conversion of Δ 4 > ‐cholesten‐3‐one to the enol acetate followed by reduction with sodium borodeuteride in a deuterated solvent yielded cholesterol‐3,4‐d 2 . Similarly Δ 4 ‐cholesten‐3‐one‐2,2,4,6,6‐d 5 obtained by base‐catalyzed exchange of Δ 4 ‐cholesten‐3‐one in ethanol‐O‐d 1 was converted to the enol acetate, followed by reduction with sodium borohydride in a deuterated medium to give cholesterol‐2,2,4,4,6‐d 5 .