571-41-5

Usage

InChI:InChI=1/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16+,17-,18+,19-/m0/s1

Synthetic route

4-(diethylamino)butan-2-one (3299-38-5) + 17β-hydroxy-desA-9β,10β-androstan-5-one + potassium tert-butylate (865-47-4) → 9β,10α-testosterone (571-41-5)

Conditions	Yield
With nitrogen In benzene

9β,10α-testosterone (571-41-5) + cyclohexanylcarbonyl chloride (2719-27-9) → Retrotestosteron 17-hexahydrobenzoat

Conditions	Yield
With pyridine In benzene

9β,10α-testosterone (571-41-5) + formic acid ethyl ester (109-94-4) → 2-Hydroxymethylenretrotestosteron

Conditions	Yield
With sodium hydride In benzene

9β,10α-testosterone (571-41-5) + methyl iodide (74-88-4) → 4,4-Me2-retroandrost-5-en-17β-ol-3-on

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol

9β,10α-testosterone (571-41-5) + methyl iodide (74-88-4) → 2-Me-retrotestosteron

Conditions	Yield
(i) (CO2Et)2, NaH, benzene, (ii) /BRN= 969135/, K2CO3, acetone, (iii) NaOEt, EtOH; Multistep reaction;

9β,10α-testosterone (571-41-5) + 3,5-dinitrobenoyl chloride (99-33-2) → Retro-5-androstan-3.17β-diol bis (3.5-(NO2)2-benzoat)

Conditions	Yield
(i) Li, liq. NH3, Et2O, (ii) /BRN= 990249/, Py, benzene; Multistep reaction;

9β,10α-testosterone (571-41-5) → 8,17β-Dihydroxy-Δ-9β,10α-androsten-3-on (23015-92-1)

Conditions	Yield
(microbiological transformation);

9β,10α-testosterone (571-41-5) → 9,17β-Dihydroxy-Δ4-9β,10α-androsten-3-on (23015-96-5)

Conditions	Yield
(microbiological transformation);

9β,10α-testosterone (571-41-5) → 11α.17β-Dihydroxy-9β.10α-androsten-4-3-on

Conditions	Yield
(microbiological transformation);

9β,10α-testosterone (571-41-5) → 9-Hydroxy-Δ4-9β,10α-androsten-3,17-dion (23015-99-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: (microbiological transformation) 2: aq. CrO3, H2SO4 / acetone View Scheme

Upstream product

• 63-05-8 androst-4-ene-3,17-dione 
• 63-05-8 4-androstene-3,17-dione 

Downstream Products

• 846-46-8 β-androstan-3,17-dion 
• 846-46-8 α-androstan-3,17-dion 
• 63-05-8 androst-3-en-3,17-dion 
• 1156-92-9 (10S,13R)-10,13-Dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol 
• 58-22-0 testosterone 

Relevant academic research and scientific papers

Biotransformation of androst-4-ene-3,17-dione by some fungi

The incubations of androst-4-ene-3,17-dione with Aspergillus candidus MRC 200634, Aspergillus tamarii MRC 72400, Aspergillus wentii MRC 200316 and Mucor hiemalis MRC 70325 for 5 days are reported. A. candidus MRC 200634 mainly hydroxylated androst-4-ene-3,17-dione at C-11α, C-15α and C-15β whilst A. wentii MRC 200316 hydroxylated it mainly at C-6β. A. tamarii MRC 72400 showed predominately a Baeyer–Villiger monooxygenase activity. M. hiemalis MRC 70325 hydroxylated the substrate at C-14α and reduced most of it at C-17.

A GENERAL METHOD FOR THE SELECTIVE REDUCTION OF KETONES IN THE PRESENCE OF ENONES.

Ketones can be reduced in the presence of conjugated enones by sodium borohydride in 50percent methanol in dichloromethane at -78 deg C.The selectivity is generally excellent.In favorable cases the reaction can be carried out at room temperature in dichloromethane with acetic acid as catalyst.