Synthesis and spectral properties of 5α-cholesta-6,8,14-trien-3β-ol

✍ Scribed by Edward J. Parish; Mitsuhiro Tsuda; George J. Schroepfer Jr.

• Book ID: 103042080
• Publisher: Elsevier Science
• Year: 1979
• Tongue: English
• Weight: 617 KB
• Volume: 25
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(79)90061-6

✦ Synopsis

Treatment of 2#-benzoyloxy-7a,15#-dichloro-5a-cholest-8( )-ene with potassium hydro-:~ide in refluxing t-butanol gave, after appropriate purification, 5a-cholesta-6,8,14-trien-3#-ol. Full characterization of the latter sterol and its 3/3-benzoate ester are described herein. Detailed '3C nuclear magnetic resonance studies of the free sterol and the benzoate ester have been completed. The assignments for each of the carbons in 5a-cholesta-6,8,14-trien-3#-ol and the benzoate ester have been made. In addition, analyses of the effects of olefinic double bonds on the 'aC chemical shifts of the angular C-18 and C-19 methyl carbons have been presented. A mechanism consistent with the formation of the A6,a,'4-triene from the 7a,15#-dichloro-AsO4)-steryl ester has been described.