title: Oxysterols: 27-hydroxycholesterol and its radiolabeled analog.
abstract: We describe a convenient and stereoselective route to the synthesis of 27-hydroxycholesterol. Also its radiolabeled analog, 22, 23 di [(3)H]-27-hydroxycholesterol with high specific radioactivity (55 Ci/mmol) was synthesized by this method. Julia condensation of steroidal 22-sulfone with aldehyde, led to the addition of the 23-27 carbon side chain building block to the steroid backbone. Formed in this reaction beta-hydroxysulfone moiety was reduced by sodium amalgam generate 22-23 unsaturated bond. Further reduction either by hydrogen or tritium furnished substrates for the synthesis of title compounds.
authors.affiliation: Albany Molecular Research, Inc., 21 Corporate Circle, Albany, NY 12203, USA.
authors.forename: T E
authors.initials: TE
authors.lastname: D'Ambra
authors.forename: N B
authors.initials: NB
authors.lastname: Javitt
authors.forename: J
authors.initials: J
authors.lastname: Lacy
authors.forename: P
authors.initials: P
authors.lastname: Srinivasan
authors.forename: T
authors.initials: T
authors.lastname: Warchol
mesh_terms: D002851:Chromatography, High Pressure Liquid; D006888:Hydroxycholesterols / Q000138:chemical synthesis* / Q000737:chemistry; D007553:Isotope Labeling / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods; D013055:Spectrophotometry, Infrared / Q000379:methods; D014316:Tritium / Q000737:chemistry
chemical_list: D006888:Hydroxycholesterols; D014316:Tritium; C076996:27-hydroxycholesterol