28398-70-1Relevant articles and documents
Acid-catalysed Rearrangements of Steroid Alkenes. Part 2. A Re-investigation of the Backbone Rearrangement of Cholest-5-ene
Peakman, Torren M.,Ellis, Karen,Maxwell, James R.
, p. 1071 - 1076 (2007/10/02)
Backbone rearrangement of cholest-5-ene (1) with boron trifluoride-diethyl ether gives, in addition to the well known diacholest-13(17)-enes (4a,b), their 10β counterparts (6a,b) as minor products.With anhydrous toluene-p-sulphonic acid-acetic acid, additional products include components also isomeric at C-10 and C-20 and having a spiro C/D ring junction.A proposed scheme for the rearrangement is given.
REACTIONS IN DRY MEDIA: REACTIONS OF CHOLESTEROL AND CHOLESTANES ON SILICA BOUND FERRIC CHLORIDE CHOLESTANE-DIACHOLESTENE REARRANGEMENT
Tal, Daniel M.,Keinaen, Ehud,Mazur, Yehuda
, p. 4327 - 4330 (2007/10/02)
Reaction of cholesterol with silica bound FeCl3 resulted in a mixture of 3β-cholesteryl chloride and dicholesteryl ether.5-cholestene and hydroxy-and halogeno-substituted cholestane derivatives gave on heating at 100 deg C with this reagent a 1:1 mixture of 20-epimeric diacholestenes.The 20(R)-isomer gave with meta-chloroperbenzoic acid 20(R)-α-epoxide, while the 20(S)-gave a mixture of 20(S)-α- and 20(S)-β-epoxides.5α,6β-Dihydrocholestane reacted with the FeCl3/SiO2 under milder conditions (50 deg C) to give 6β-hydroxy-20(R)-diacholestene, which was converted to the 20(R)-diacholestene.
