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ChemicalBook CAS DataBase List 1-((3R,5R,8R,9R,10S,13S,14S,17S)-3-hydroxy-3,13-diMethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone

1-((3R,5R,8R,9R,10S,13S,14S,17S)-3-hydroxy-3,13-diMethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone synthesis

6synthesis methods
(3R,5R,8R,9R,10S,13S,14S,17S)-17-(1-hydroxyethyl)-3,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-ol

1430063-92-5
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1-((3R,5R,8R,9R,10S,13S,14S,17S)-3-hydroxy-3,13-diMethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone

162882-77-1
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Yield:162882-77-1 90 mg

Reaction Conditions:

with Dess-Martin periodane in dichloromethane at 20; for 24 h;

Steps:

1 Synthesis of compound 8b

[00328] Synthesis of compound 8b. To a solution of crude compound 7b (200 mg) was dissolved in 10 mL of H20 saturated dichloromethane (dichloromethane had been shaken with several milliliters of H20 then separated from the water layer) was added Dess-Martin periodinate (400 mg, 0.94 mmol). After stirring at room temperature for 24 h, the reaction mixture was extracted with dichloromethane (3 x 10 mL). The combined organic layers were washed with 10 % aqueous Na2S203 (10 mL), brine (10 mL), dried over MgS04, filtered, and concentrated. The residue was purified by chromatography on silica gel (pertroleum ether/ ethyl acetate = 4: 1 to 2: 1) to afford title compound 8b (90 mg, 0.28 mmol, 57% for two steps) as a white solid. 1H NMR (400 MHz, CDC13), δ (ppm), 2.55-2.51 (m, 1H), 2.11 (S, 3H), 1.32 (S, 3H), 0.61(S, 3H).

References:

WO2013/56181,2013,A1 Location in patent:Paragraph 00328