5692-03-5

Upstream product

• 481-30-1 epitestosterone 
• 17291-35-9 3-Oxo-5α-androstan-17β-ol-toluol-p-sulfonat 
• 71120-50-8 Pyridine-3-sulfonic acid (5S,10S,13S,17S)-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester 
• 396079-66-6 17α-benzoyloxy-5β-androstanone-(3) 
• 481-30-1 epitestosterone 
• 150054-85-6 3-oxo-5β-androstan-17α-yl cyclohexanecarboxylate 
• 1259-22-9 5-androstene-3β,17β-diol 3-acetate 17-p-toluene-δ-sulfonate 
• 36025-82-8 3-oxoandrost-4-en-17α-yl benzoate 
• 853-23-6 prasterone acetate 
• 40768-04-5 3β-hydroxyandrost-5-en-17α-yl benzoate 
• 150054-84-5 Cyclohexanecarboxylic acid (3S,5R,8R,9S,10S,13S,14S,17R)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester 
• 40768-03-4 androst-5-ene-3β,17α-diyl 3-acetate 17-benzoate 
• 1639-43-6 androstenediol-3-acetate 
• 100428-85-1 17α-hydroxyandrost-5-en-3β-yl 3-acetate 

Downstream Products

• 64919-12-6 dihydrotestosterone p-chlorophenoxyisobutyrate 
• 88674-60-6 2-(4-Chloro-phenoxy)-2-methyl-propionic acid (5S,10R,13S,17S)-3-[2-(4-chloro-phenoxy)-2-methyl-propionyloxy]-10,13-dimethyl-2,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 
• 855-22-1 dihydrotestosterone propionate 
• 88674-61-7 Propionic acid (5S,10R,13S,17S)-10,13-dimethyl-17-propionyloxy-2,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 17006-60-9 3α-ethynyl-3β-hydroxyandrostan-17-one 
• 1408057-15-7 3-oxo-5β-androstan-17α-yl pentafluorobenzoate 
• 1408057-20-4 17α-(pentafluorobenzoyl)oxy-5β-androstan-3α-yl sulfate pyridinium salt 
• 1408057-18-0 5β-androstane-3α,17α-diyl 17-(pentafluorobenzoate) 3-(L-glutamate) 
• 1408057-17-9 5β-androstane-3α,17α-diyl 17-(pentafluorobenzoate) 3-[O⁵-tert-butyl-N-(tert-butoxycarbonyl)-L-glutamate] 
• 1408057-16-8 3α-hydroxy-5β-androstan-17α-yl pentafluorobenzoate 
• 1321605-19-9 3-oxo-5β-androstan-17α-yl tosylate 
• 10148-98-8 (3S,5S,8R,9S,10S,13S,14S,17S)-3-ethynyl-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol 
• 65-06-5 17-Hydroxy-androst-1-en-3-on 

Relevant academic research and scientific papers

Distinction Between 17-Epimeric Hydroxy Steroids of the 3,17-Dioxygenated Androstane Series by Chemical Ionization

The distinction between 17-epimeric 3,17-dioxygenated hydroxyandrostanes has been made by comparison of both their methane or ammonia positive and OH- negative chemical ionization (CI) mass spectra.In the methane or ammonia positive CI, the 17α-configuration in the eight stereoisomeric 5ξ-androstane-3ξ,17ξ-diols can be determined by the relative abundances of the ion +.In the ammonia CI spectra, the ion + possesses only a low abundance, but a comparison of the relative rates of the loss of water v. the loss of ammonia from + in the second field -free region allows a clear distinction to be made between the 17α- and 17β-series.In the OH- negative CI mass spectra, the 5ξ-androstane-3-one-17ξ-ols produce an intense ion - in the 17α-series only.

Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH3CN

A mild process using a combination of TMSCl and NaI in acetonitrile is used to regenerate carbonyl compounds from a variety of dithiane and dithiolane derivatives. This easy to handle and inexpensive protocol is also efficient to deprotect oxygenated and mixed acetals as 1,3-dioxanes, 1,3-dioxolanes and 1,3-oxathianes quantitatively. As a possible extension of this method, it was also shown that nitrogenated substrates such as hydrazones, N-tosylhydrazones, and ketimines reacted well under these conditions to give the expected ketones in high yields. The methodology proposed herein is a good alternative to the existing methods since it does not use metals, oxidants, reducing agents, acidic or basic media, and keto-products were obtained in high to excellent yields.

Steroidal isomers with uniform mass spectra of their per-TMS derivatives: Synthesis of 17-hydroxyandrostan-3-ones, androst-1-, and -4-ene-3,17-diols

In human sports doping control analysis most of the steroids are analyzed after enzymatic hydrolysis of the glucuronides as per-trimethylsilyl (TMS) derivatives applying gas chromatography-mass spectrometry (GC-MS). According to the recommendations of the World Anti-Doping Agency the identification of analytes should be based on retention time and on mass spectrometric characterization. This study shows that the bis-TMS derivatives of 16 specific C19 steroids, namely the stereoisomers of 5ξ-androst-1-ene-3ξ,17ξ-diol (8 isomers), androst-4-ene-3ξ,17ξ-diol (4 isomers), and 17ξ-hydroxy-5ξ-androstan-3-one (4 isomers), reveal very similar mass spectra. As a rule, when taking the retention times, which are provided as Kovac indices for all these isomers, into account, a restriction to two or three possible isomers is possible. Reliable identification should additionally include a comparison of the retention times of the analytes with the reference compounds measured concomitantly. In some cases standard addition may be appropriate. Due to the limited availability, the above mentioned isomers were synthesized by reduction of the corresponding α,β-unsaturated oxo steroids either with K-Selectride or by catalytic hydrogenation (Pd/C as catalyst). The products of the reactions were identified by means of nuclear magnetic resonance (NMR) characterization and by further reduction to the corresponding 5ξ-androstane-3ξ,17ξ-diols and GC-MS comparison with commercially available reference standards.

PREPARATION OF UNLABELLED AND 3H>-LABELLED EPITESTOSTERONE AND ITS METABOLITES

Cold as well as 3H>-labelled substrates and metabolites IX-XI, XV, XVI, XX-XXII, XXIV, XXV and XXVIII were prepared by catalytic hydrogenation of epitestosterone (VIII) and Λ1-dehydroepitestosterone (XIII).The key step in the preparation of compound XXVIII was reaction of 3β-tosylates XXVI and XXX with potassium nitrite in dimethyl sulfoxide.