103708-01-6

Upstream product

• 434-64-0 perfluorotoluene 
• 63-05-8 Androstenedione 

Downstream Products

• 154229-37-5 3-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>androsta-3,5,16-trien-17-yl trifluoromethanesulfonate 
• 77546-39-5 <16,16,17α-(2)H3> testosterone 
• 154229-38-6 3-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-17-(3-pyridyl)androsta-3,5,16-triene 
• 154229-21-7 17-(3-pyridine)-4,16-dieneandrost-3-one 
• 103708-02-7 3-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy><16,16,17α-(2)H3>androsta-3,4-diene-17β-ol 
• 63-05-8 Androstenedione 

Relevant academic research and scientific papers

Heptafluoro-p-tolyl as a Selective Protecting Group for the Enone Function of Androst-4-ene-3,17-dione: Application to the Preparation of Deuterium-labelled Testosterone

Octafluorotoluene reacts with the enone function of androst-4-ene-3,17-dione in the presence of caesium fluoride to give specifically a 3,5-dienol ether which has been used to prepare deuterium-labelled testosterone.

The Selective Protection of the 3-Ketone Functions of Steroids as Heptafluoro-p-tolyl Enol Ethers

Conjugated and unconjugated 3-ketone functions in steroids react with octafluorotoluene at above 100 deg C in the presence of caesium fluoride to give heptafluoro-p-tolyl enol ethers.The related but unusually reactive Wieland-Miescher ketone (11) reacted at room temperature in the presence of tetra-n-butylammonium fluoride.Enones were regenerated from their derivatives by acidic hydrolysis.Hydrolysis of the derivative (10) of 4,5α-dihydroxytestosterone was slu but sodium methoxide regenerated the parent steroid.The methods have been applied in a synthesis of deuterium-labelled testosterone.