514-17-0

Usage

InChI:InChI=1/C19H30O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h11-15,17,20-21H,3-10H2,1-2H3

Upstream product

• 516-39-2 5α-pregnane-3β,11β,17,20β_F,21-pentaol 
• 1856-12-8 21-acetoxy-3β,17-dihydroxy-5α-pregnane-11,20-dione 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 50-23-7 HYDROCORTISONE 
• 26341-19-5 11β-formyloxyandrost-4-ene-3,17-dione 
• 382-44-5 (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione 
• 67-56-1 methanol 
• 75585-75-0 11β-formyloxy-3β-hydroxy-5α-androstan-17-one 
• 651-43-4 5α-pregnane-3β,11β,17α,21-tetraol-20-one 
• 68678-50-2 3β,11β,17-trihydroxy-21-nor-5α-pregnanoic acid-(20) 
• 481-29-8 Epiandrosterone 
• 75585-73-8 11β-formyloxy-5α-androstane-3,17-dione 

Downstream Products

• 2136-21-2 17-methyl-5α-androstane-3β,11β,17β-triol 
• 5953-59-3 3β,11β-dihydroxy-5α-androstanone-(17)-semicarbazone 
• 1429-06-7 5α-androstane-3,11,17-trione 
• 4731-15-1 3β-acetoxy-5α-androstanedione-(11.17) 
• 32693-29-1 3β,16β-Dihydroxy-5α-androstan-11-on 
• 5424-40-8 3β,17β-diacetoxy-5α-androstane 
• 57-61-4 (3R,5S,8S,9S,10S,11S,13S,14S)-3,11-dihydroxy-10,13-dimethyl-tetradecahydro-2H-cyclopenta[a]phenanthren-17(14H)-one 
• 115484-96-3 11β-hydroxy-3β-(toluene-4-sulfonyloxy)-5α-androstan-17-one 

Relevant academic research and scientific papers

Baeyer-villiger oxidation of some steroids by Aspergillus tamarii MRC 72400

Biotransformations of epiandrosterone (1), dehydroepiandrosterone (2), testosterone (3), progesterone (4) and pregnenolone (5) by Aspergillus tamarii MRC 72400 for 5 days have been reported and the results of these incubations have been compared with previously published data obtained with Aspergillus tamarii QM 1223. A. tamarii MRC 72400 showed higher Bayer-Villiger monooxygenase activities than A. tamarii QM 1223 did. Apart from pregnenolone (5), A. tamarii MRC 72400 metabolized these steroids in different ways. Incubation of epiandrosterone (1) afforded 3β,11β-dihydroxy-5α-androstan-17- one (6) (3%) and 3β-hydroxy-17a-oxa-D-homo-5α-androstan-17-one (7) (9.5%). Incubation of dehydroepiandrosterone (2) afforded 3β-hydroxy-17a- oxa-D-homoandrost-5-en-17-one (8) (28%), testolactone (9) (6%), 3β,7β-dihydroxyandrost-5-en-17-one (10) (13%) and 3β,7α- dihydroxyandrost- 5-en-17-one (11) (24%). Incubation of testosterone (3) afforded testolactone (9) (58%). Incubation of progesterone (4) also afforded testolactone (9), however in higher yield (86%). Incubation of pregnenolone (5) afforded 3β-hydroxy-17a-oxa-D-homoandrost- 5-en-17-one (8) (25%) and testolactone (9) (27%).

SYNTHESIS OF 11-HYDROXYLATED ANDROSTANE DERIVATIVES

Reaction conditions for selective reductions of 3- and 17-oxo groups are described and applied to syntheses of 11-hydroxylated derivatives.