18167-94-7Relevant articles and documents
Preparation method of oxandrolone intermediate
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Paragraph 0039; 0040, (2021/07/01)
The invention belongs to the technical field of organic synthesis, and provides a preparation method of 17[beta]-hydroxy-17[alpha]-methyl-1-oxo-1,2-open-loop-A-nor-5[alpha]-androstane-2-oxygen-containing carboxylic acid. The preparation method comprises the following steps: 1) mixing mestanolone, 2-iodoxybenzoic acid, a catalyst and a solvent, and then carrying out an oxidation reaction to obtain a compound 1; and 2) mixing the compound 1, an aqueous solution of an oxidizing agent, bicarbonate and acetone, and then carrying out an oxidation reaction so as to obtain the 17[beta]-hydroxy-17[alpha]-methyl-1-oxo-1,2-open-loop-A-nor-5[alpha]-androstane-2-oxygen-containing carboxylic acid. The purity of the intermediate obtained by the preparation method is greater than or equal to 98%, and the yield is 95-97%; and the preparation method disclosed by the invention is low in required reaction temperature, short in product production period, simple to operate, low in production cost, friendly to environment, and reaction time is remarkably shortened.
Characterization of desoxymethyltestosterone main urinary metabolite produced from cultures of human fresh hepatocytes
Gauthier, Julie,Poirier, Donald,Ayotte, Christiane
, p. 635 - 643 (2012/06/01)
Desoxymethyltestosterone (DMT; 17β-hydroxy-17α-methyl-5α- androst-2-ene) is a designer steroid present in hormonal supplements distributed illegally as such or in combination with other steroids, for self-administration. It figures on the list of substances prohibited in sports and its detection in athlete's urine samples is based upon the presence of the parent compound or the main urinary metabolite, which has not been characterized yet. Following its isolation from cultures of human fresh hepatocytes and S9 fractions of liver homogenates, we were able to identify this metabolite as being 17α-methyl-2β,3α,17β-trihydroxy-5α-androstane. Other minor metabolites were also characterized. The production, isolation, NMR, mass spectral analyses and chemical synthesis are presented.
Efficient oxidizing methods for the synthesis of oxandrolone intermediates
Ginotra, Sandeep K.,Chhikara, Bhupender S.,Singh, Manish,Chandra, Ramesh,Tandon, Vibha
, p. 989 - 991 (2007/10/03)
Mild, efficient and eco-friendly oxidation of 17α-methylandrostan- 3β-17β-diol (1) has been studied with three different reagents viz. pentavalent iodine reagent 2-iodoxy benzoic acid (IBX) in DMSO at 65°C, sodium hypochlorite and H2O2/Na2WO4 under phase transfer conditions to give 17β-hydroxy-17α- methylandrostan-3-one (mestanolone 2), a drug intermediate as oxidized product. The H2O2/Na2WO4/PTC gave mestanolone in high yield and purity whereas sodium hypochlorite/PTC system yielded some chlorinated material along with the mestanolone. However, 1 with 2.5 equivalent of IBX gave 17β-hydroxy-17α-methyl- Δ1-androsten-3- one (3) under the similar reaction conditions in good yield and single step reaction.
