7α,12α-Dihydroxy-5β-cholestan-3-one synthesis
- Product Name:7α,12α-Dihydroxy-5β-cholestan-3-one
- CAS Number:547-97-7
- Molecular formula:C27H46O3
- Molecular Weight:418.65
120174-41-6
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547-97-7
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Yield:547-97-7 90%
Reaction Conditions:
with water;potassium hydroxide in methanol at 30; for 16 h;
Steps:
3.14 3.3.14 7α,12α-Dihydroxy-5β-cholestan-3-one (10a)
3-oxo-7,12-diacetate 9a (200 mg, 0.40 mmol) was completely hydrolyzed in 10% methanolic KOH (3.5 g) at 30 °C for 16 h. Most of the solvent was evaporated off, and the residue was dissolved in water and acidified with 10% HCl with stirring and ice-bath cooling. The precipitate was collected by filtration and washed with water. Recrystallization from methanol gave the 7,12-dihydroxy-3-one 10a as colorless thin plates; yield, 149 mg (90%); mp, 195-197 °C (literature value: mp, 209-210 °C) [21]. 1H-NMR (500 MHz, CDCl3): δ = 0.74 (s, 3H, 18-H3), 0.86 (d, 3H, J = 6.0 Hz, 27-H3), 0.87 (d, 3H, J = 6.0 Hz, 26-H3), 0.98 (d, 3H, J = 6.5 Hz, 21-H3), 1.00 (s, 3H, 19-H3), 3.93 (brs, 1H, 7β-H), 4.06 (brs, 1H, 12β-H). 13C-NMR (125.8 MHz, CDCl3): δ = 12.6 (C-18), 17.8 (C-21), 21.7 (C-19), 22.5 (C-26), 22.8 (C-27), 23.1 (C-23), 23.8 (C-15), 27.3 (C-9), 27.5 (C-16), 28.0 (C-25), 28.5 (C-11), 33.7 (C-6), 34.9 (C-10), 35.4 (C-20), 36.0 (C-22), 36.6 (C-1), 36.8 (C-2), 39.4 (C-24), 39.6 (C-8), 41.9 (C-14), 43.1 (C-5), 45.6 (C-4), 46.6 (C-13), 47.7 (C-17), 68.3 (C-7), 72.9 (C-12), 213.1 (C-3). HR-APCI-MS, calcd. for C27H45O3 [M-H]-, 417.3369; found, 417.3361.
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]
81-25-4
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547-97-7
15 suppliers
$175.00/1mg
52840-09-2
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20171-56-6
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547-97-7
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87899-19-2
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547-97-7
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