209850-50-0

Upstream product

• 563-80-4 3-methyl-butan-2-one 
• 103751-19-5 (3β,5α,22E)-3-(benzoyloxy)-4,4-dimethylergosta-8(14),22-dien-15-one 
• 117438-96-7 Benzoic acid (3S,5R,9R,10R,13R,17R)-17-((E)-(R)-1,5-dimethyl-4-oxo-hex-2-enyl)-4,4,10,13-tetramethyl-15-oxo-2,3,4,5,6,7,9,10,11,12,13,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 209850-48-6 Benzoic acid (3S,5R,9R,10R,13R,17R)-17-((S)-2-hydroxy-1,5-dimethyl-4-oxo-hexyl)-4,4,10,13-tetramethyl-15-oxo-2,3,4,5,6,7,9,10,11,12,13,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117438-93-4 (3β,5α,20S)-3-(Benzoyloxy)-4,4-dimethyl-15-oxopregn-8,14-ene-20-carboxaldehyde 
• 117438-97-8 3β-(Benzoyloxy)-4,4-dimethyl-5α-cholest-8(14)-ene-15,24-dione 

Downstream Products

• 7408-47-1 4,4-Dimethylzymosterol benzoate 
• 7448-02-4 4,4-dimethyl-5α-cholesta-8,24-dien-3β-ol 
• 64284-64-6 4,4-DIMETHYL-5ALPHA-CHOLESTA-8,14,24-TRIENE-3BETA-OL 
• 117168-35-1 Benzoic acid (3S,5S,10S,13R,14R,17R)-17-((E)-(R)-1,5-dimethyl-hex-3-enyl)-10,13-dimethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117439-08-4 Benzoic acid (3S,5R,10S,13R,17R)-17-((R)-1,5-dimethyl-hex-4-enyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117439-18-6 Benzoic acid (3S,5R,10S,13R,14R,17R)-17-((R)-4-hydroxy-1,5-dimethyl-hexyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117439-14-2 Benzoic acid (3S,5R,10S,13R,14R,15S,17R)-17-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-hexyl]-15-hydroxy-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117439-16-4 Benzoic acid (3S,5R,10S,13R,14R,17R)-17-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-hexyl]-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117439-09-5 Benzoic acid (3S,5R,10S,13R,17R)-17-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-hexyl]-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117438-85-4 (3β,5α,24R,S)-4,4-Dimethylcholesta-8,14-diene-3,24-diol 3-benzoate 24-trifluoroacetate 
• 117439-06-2 Benzoic acid (3S,5R,10S,13R,17R)-17-[(R)-1,5-dimethyl-4-(2,2,2-trifluoro-acetoxy)-hexyl]-4,4,10,13-tetramethyl-15-trifluoromethanesulfonyloxy-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117438-89-8 (3β,5α,24R,S)-3-(Benzoyloxy)-4,4-dimethyl-24-(trifluoroacetoxy)cholest-8(14)-en-15-one 

Relevant academic research and scientific papers

Meiosis regulating compounds

Certain compounds, structurally related to natural compounds which can be extracted i.a. from bull testes and from human follicular fluid, can be used for regulating the meiosis in oocytes and in male germ cells. Some of these compounds are useful in the treatment of infertility, whereas other compounds are useful as contraceptives. These compounds have the structural formula wherein the substituents are as defined in the specification.

Synthesis of zymosterol, fecosterol, and related biosynthetic sterol intermediates

The first syntheses of sterol biosynthetic intermediates zymosterol(4), 4,4-dimethylzymosterol(5), cholesta-8,14,24-trien-3β-ol(6), the 4,4-dimethyl analogue 7, and fecosterol (8) are described in detail. Multigram quantities of key intermediates 16 and 17 were efficiently prepared from known enones 20 and 21 (eight steps, 35% overall yield). Novel entry into Δ8-sterols was achieved through regiospecific hydroboration/deoxygenation of the 8,14-diene systems. Sterols containing Δ24- or Δ(24(28))-olefins were obtained from C24-hydroxy intermediates either via dehydration using bis[α,α-bis(trifluoromethyl)benzenemethanolato]diphenylsulfur in CH2Cl2 or via Swern oxidation/Wittig olefination, respectively. In this way, 16 and 17 were converted to the desired Δ8,24-, Δ8,14,24-, and Δ(8,24(28))-sterols with high regiocontrol.