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ChemicalBook CAS DataBase List Boldenone

Boldenone synthesis

8synthesis methods
Boldenone is obtained by reacting Testosterone with tert-butyldimethylsilyl chloride in the presence of DDQ.
Experimental Procedure: 29.0 g Testosterone was dissolved in 220 ml dioxan/THF 8:2 and cooled to 0°C on ice. After cooling down a solution of tert-butyldimethylsilyl chloride (46.0 g in 100 ml dioxan/THF 8:2) was added dropwise and stirred for 90 min at 0°C. Then a suspension of 32.0 g of DDQ in 200 ml dioxan/THF 8:2 was added in 4 equal portions over a period of 4 h. The reaction mixture was stirred for additional 12 h within coming from 0°C to room temperature. The resulting suspension was then filtered over Celite and rinsed with 300 ml THF. The filtrate was evaporated and brown oil was obtained. The oil was diluted in 1500 ml DCM and washed with 500 ml of 5% aqueous sodium hydroxide. The yellow organic phase was washed with 400 ml water and 400 ml saturated sodium chloride solution, before drying over magnesium sulfate. After evaporation, the crude product was chromatographed on silica gel by using hexane-ethyl acetate (3:7), followed by a recrystallization in ethyl acetate. 16.50 g of Boldenone was obtained as an amber solid (58%).
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Yield:-

Steps:

Multi-step reaction with 3 steps
1: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction
2: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction
3: unidentified fungal species isolated from grinded corn / water / 1 h / 37 °C / pH 7 / aq. phosphate buffer; Microbiological reaction; Enzymatic reaction

References:

Verheyden;Noppe;Zorn;Van Immerseel;Bussche, J. Vanden;Wille;Bekaert;Janssen;De Brabander;Vanhaecke [Journal of Steroid Biochemistry and Molecular Biology,2010,vol. 119,# 3-5,p. 161 - 170]

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