ChemicalBook CAS DataBase List DELTA-4,6-CHOLESTADIENOL (30 MG)

DELTA-4,6-CHOLESTADIENOL (30 MG) synthesis

7synthesis methods

Product Name:DELTA-4,6-CHOLESTADIENOL (30 MG)
CAS Number:14214-69-8
Molecular formula:C27H44O
Molecular Weight:384.64

3464-60-6 Synthesis

3464-60-6
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14214-69-8
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Yield:14214-69-8 73%

Reaction Conditions:

with sodium tetrahydroborate in ethanol at 20; for 18 h;

Steps:

Synthesis of Cholest-4,6-diene-3-ol (12):
To a solution of 11 (1 g, 2.63 mmol) in absolute ethanol (30 mL) at room temperature, NaBH₄ (393 mg, 10.4 mmol) was added dropwise. Then the mixture was stirred at room temperature and the reaction progress was checked by TLC analysis. When the reaction was complete after 18 h, the solvent was removed under reduced pressure, and water (15 mL) was added to the residue, which was stirred for 0.5 h at room temperature. The mixture was then extracted with DCM (3×40 mL). Finally, the combined organic phase was dried over anhydrous Na₂SO₄, concentrated in vacuo, and purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (4:1, v/v) to afford 12 in a 73% yield as a white solid. mp = 114-116 ^oC. IR cm^-1 (KBr): 3374, 3019, 2937, 2866, 1641, 1467, 1381, 1288, 1025. ¹H NMR (400 MHz, CDCl₃) δ: 5.88 (dd, J = 2.4, 10.0 Hz, 1H), 5.62 (d, J = 9.6 Hz, 1H), 5.35 (s, 1H), 4.25-4.32 (m, 1H), 1.99-2.08 (m, 3H), 1.83-1.88 (m, 1H), 1.72-1.76 (m, 1H), 1.61-1.68 (m, 3H), 1.44-1.53 (m, 3H), 1.25-1.35 (m, 6H), 1.09-1.16 (m, 6H), 0.98-1.03 (m, 5H), 0.90 (d, J = 6.4 Hz, 3H), 0.87 (d, J = 1.6 Hz, 3H), 0.85 (d, J = 1.6 Hz, 3H), 0.72 (s, 3H).

References:

Yang, Chun;Shao, Yonghua;Zhi, Xiaoyan;Huan, Qu;Yu, Xiang;Yao, Xiaojun;Xu, Hui [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 17,p. 4806 - 4812] Location in patent:supporting information

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