54446-73-0Relevant academic research and scientific papers
Further studies on the synthesis of 24(S),25-epoxycholesterol. A new, efficient preparation of desmosterol
Spencer, Thomas A.,Li, Dansu,Russel, Jonathon S.,Tomkinson, Nicholas C. O.,Willson, Timothy M.
, p. 1919 - 1923 (2000)
Efforts to improve the synthesis of 24(S),25-epoxycholesterol (1) from stigmasterol (3) have included identification of 6α-hydroxy-i-steroid 11 as a byproduct from the ozonolysis of 9 and an attempt to effect conversion of sulfone 14 to diol 18 via Payne rearrangement and nucleophilic trapping of epoxide 25, which led instead to 27 and 28 (97% yield). A more efficient synthesis of 1 was achieved via coupling of cuprate 21 with allylic acetate 31 to give 73% of 16, in the most efficient conversion yet of a C22 intermediate to desmosterol (5) or its acetate 6.
