Synthesis of stereospecifically labelled [4-3H]cholesterol

✍ Scribed by W. J. S. Lockley; H. H. Rees; T. W. Goodwin

• Publisher: John Wiley and Sons
• Year: 1978
• Tongue: French
• Weight: 352 KB
• Volume: 15
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580150148

✦ Synopsis

HlCholesterol was prepared in three steps from 4-0xo-cholerrt-5-en-39-y1 acetate, which warn conveniently prepared f r o m cholesterol. Introduction of the h y H label utiliwd N d Y a8 the .wTce Of tritium. Iktail6 0 this 6ytIthe6i6 and a l m the amthesf8 of [+YH f cholesterol are given. ~ocedurctrn for quantitative estimation of the tritium label at the h and 48 positions are a l m described. Key word68 [h-' H'lcholesterol, [49-yH]cholesteml, 4-oxo-cholest-5-en-39-yl acetate. MTIMDUCTIW Metabolic modification of the A and B ring8 of steroids frequently involves mtereoupecific removal of a hydrogen from C-4 of cholesterol with formation of a A ' bond. metabolic transformations often necessitates the availability of both C ~Z -~H I and [k$-Hlcholesterol arbstratee. The preuent paper reports the synthesis of [h?Hlcholesterol; 8Ynthesis of 148-HI&ole&ero1 is only outlined briefly, since the reactions for the introduction of imtope at the 4p-position have been described previously Investigation of such I Y