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18162-48-6872-50-4Methylene ChloridenaphthaleneTHFTitanium Dioxide
ChemicalBook CAS DataBase List (7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one synthesis

8synthesis methods
Cholest-4-en-3-one, 7-(formyloxy)-, (7α)-

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(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

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Yield: 78%

Reaction Conditions:

with water;sodium hydroxide for 0.5 h;

Steps:

3.21 3.3.21 7α-Hydroxy-4-cholesten-3-one (1b)
The 3-oxo-Δ4-diformate 12b (100 mg, 0.23 mmol) in THF (5 mL) was hydrolyzed with 0.8% aqueous NaOH, followed by acidification with 10% HCl as described for the preparation of 1a. After being processed analogously, the crude product dissolved in benzene was purified using a column of silica gel (5 g), and eluting with EtOAc-hexane (3:7, v/v). Recrystallization from methanol gave the 3-oxo-Δ4-7-hydroxy compound 1b as colorless needles; yield, 73 mg (78%); mp, 180-182 °C (literature value: mp, 183-184 °C) [23]. 1H-NMR (500 MHz, CDCl3): δ = 0.71 (s, 3H, 18-H3), 0.89 (d, 3H, J = 6.8 Hz, 27-H3), 0.90 (d, 3H, J = 6.8 Hz, 26-H3), 0.91 (d, 3H, J = 5.4 Hz, 21-H3), 1.20 (s, 3H, 19-CH3), 3.97 (brs, 1H, 7β-H), 5.80 (s, 1H, 4-H). 13C-NMR (125.8 MHz, CDCl3): δ = 11.8 (C-18), 17.0 (C-19), 18.6 (C-21), 20.8 (C-11), 22.5 (C-26), 22.8 (C-27), 23.5 (C-23), 23.7 (C-15), 28.0 (C-25), 28.1 (C-16), 33.9 (C-2), 35.3 (C-1), 35.7 (C-20), 36.0 (C-22), 38.4 (C-10), 39.1 (C-6), 39.4 (C-24), 39.7 (C-8), 40.9 (C-12), 42.4 (C-13), 45.1 (C-9), 50.4 (C-14), 55.9 (C-17), 68.4 (C-7), 126.7 (C-4), 168.0 (C-5), 198.9 (C-3). HR-ESI-MS, calcd. for C27H43O2 [M-H]-, 399.3263; found 399.3280.

References:

Ogawa, Shoujiro;Zhou, Biao;Kimoto, Yusuke;Omura, Kaoru;Kobayashi, Akiko;Higashi, Tatsuya;Mitamura, Kuniko;Ikegawa, Shigeo;Hagey, Lee R.;Hofmann, Alan F.;Iida, Takashi [Steroids,2013,vol. 78,# 9,p. 927 - 937]

Cholest-4-en-3-one, 7-(formyloxy)-, (7α)-

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4,6-CHOLESTADIEN-3-ONE

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(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

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$259.00/1mg

References
Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

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References
Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

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(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

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References
5-CHOLESTEN-3-BETA, 7-ALPHA-DIOL

566-26-7
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(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

3862-25-7
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$259.00/1mg

References

(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Related Search:

CHOLEST-4-ENE