(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester Chemical Properties

Boiling point:

540.0±50.0 °C(Predicted)

Density 

1.137

storage temp. 

2-8°C

pka

14.70±0.70(Predicted)

(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester Usage And Synthesis

Synthesis

Using (R)-methyl 4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthracenecarbonyl17-yl)valerate as a starting material, the methyl ester (2) was first obtained by protection of the hydroxyl group of the cholate. Subsequently, the methyl ester (2) was oxidized to the corresponding ketone (3) using N-bromosuccinimide (NBS). Next, the ketone (3) was protected as diacetate (4) and converted to the key intermediate bromide (5) by reaction with molecular bromine. Afterwards, the bromide (5) was hydrolyzed to produce the hydroxyketone (6). Finally, the target product (R)-4-((3R,5S,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid methyl ester (7) was obtained by reduction of acetate and methyl ester portions and full deprotection.

References

[1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 14-15, p. 2821 - 2828
[2] Journal of the Chemical Society, Chemical Communications, 1993, # 19, p. 1469 - 1471
[3] Patent: WO2011/22838, 2011, A1. Location in patent: Page/Page column 37
[4] Journal of Biological Chemistry, 1943, vol. 147, p. 131,133
[5] Steroids, 1993, vol. 58, # 2, p. 52 - 58

(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-oic acid methyl ester(10538-65-5)Related Product Information

• 12-(Acetyloxy)-3,6,7-trihydroxycholan-24-oic acid methyl ester
• 3α,12α-Diacetoxy-7-oxo-5β-cholan-24-oic acid methyl ester
• 12-(Acetyloxy)-3,6-dihydroxy-7-oxocholan-24-oic acid methyl ester
• 7-KETODEOXYCHOLIC ACID
• (3alpha,5beta,6alpha,12alpha)-3,12-Bis(acetyloxy)-6-bromo-7-oxocholan-24-oic acid methyl ester