20835-91-0Relevant academic research and scientific papers
Efficient trans-diaxial hydroxylation of Δ5-steroids
Carvalho, Jo?o F.S.,Silva, M. Manuel Cruz,Sá e Melo, M. Luisa
experimental part, p. 2455 - 2462 (2010/06/14)
A convenient, fast, and high-yielding process to synthesize 5α,6β-dihydroxysteroids directly from the correspondent Δ5-steroids is reported. The reaction protocol consists in the conjugation of a readily available and stable oxidant, magnesium bis(monoperoxyphthalate) hexahydrate, with the non-toxic bismuth(III) triflate in acetone to afford the trans-diaxial hydroxylation product in a stepwise manner and in excellent yields.
Synthesis, isolation and characterisation of β-sitosterol and β-sitosterol oxide derivatives
McCarthy, Florence O.,Chopra, Jay,Ford, Alan,Hogan, Sean A.,Kerry, Joe P.,O'Brien, Nora M.,Ryan, Eileen,Maguire, Anita R.
, p. 3059 - 3065 (2007/10/03)
β-Sitosterol is the most prevalent plant cholesterol derivative (phytosterol) and can undergo similar oxidation to cholesterol, leading to β-sitosterol oxides. The biological impact of phytosterol oxides has only been evaluated in a phytosterol blend (usually of β-sitosterol, campesterol, stigmasterol and dihydrobrassicasterol). The lack of pure phytosterols, including β-sitosterol, hinders the collection of significant toxicity data on the individual β-sitosterol oxides. An efficient synthetic route to multi-gram quantities of pure β-sitosterol is described here, together with the first syntheses and characterisation of pure β-sitosterol oxides. The Royal Society of Chemistry 2005.
Gram-scale chromatographic purification of β-sitosterol: Synthesis and characterization of β-sitosterol oxides
Zhang, Xin,Geoffroy, Philippe,Miesch, Michel,Julien-David, Diane,Raul, Francis,Aoude-Werner, Dalal,Marchioni, Eric
, p. 886 - 895 (2007/10/03)
An effective purification method for β-sitosterol was developed starting from a commercial source of a phytosterol mixture using preparative adsorption column chromatography. β-Sitosterol (≥95% purity) was obtained on a gram-scale. Thus, the synthesis of six β-sitosterol oxides, including 7α-hydroxy, 7β-hydroxy, 5,6α-epoxy, 5,6β-epoxy, 7-keto, and 5α,6β-dihydroxysitosterol, were successfully carried out. The spectral characteristics of all the synthetic intermediates and target compounds (～95% purity) were well-documented.
SYNTHESIS OF NATURAL PHYTOSTEROIDS OF THE 6-KETOSTIGMASTANE SERIES AND COMPOUNDS RELATED TO THEM
Kovganko, N. V.,Kashkan, Zh. N.
, p. 656 - 660 (2007/10/02)
Preparative methods of synthesizing a number of natural 6-ketosteroids and 6-alcohols related to them from β-sitosterol have been developed.
