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ChemicalBook CAS DataBase List 7α,25-dihydroxy Cholesterol
64907-22-8

7α,25-dihydroxy Cholesterol synthesis

3synthesis methods
-

Yield:64907-22-8 81%

Reaction Conditions:

with methanol;potassium hydroxide for 4 h;Reflux;Inert atmosphere;

Steps:

Cholest-5-ene-3β,7α,-triol (5)

The dibenzoate 4 (20 mg, 0.032 mmol) was dissoved in MeOH (1 mL) and a solution of KOH (0.5g) in MeOH (5 mL) was added. The solution was refluxed for 4 h when TLC indicated complete hydrolysis. After cooling to room temperature, MeOH was evaporated under reduced pressure and water (15 mL) was added. The mixture was extracted with ethyl acetate (4 x 25 mL). The combined organic layers were washed with brine and dried over MgSO4. After filtration, and evaporation of solvents, the crude product was purified by column chromatography (ethyl acetate-hexanes) to yield the 7,25-dihydroxycholesterol 5 as a white solid, 12 mg, (81%). Mp 235-236 oC (lit1 234 -235 oC). Spectroscopic data matched previously reported data1.

References:

Deng, Xiaohu;Sun, Siquan;Wu, Jiejun;Kuei, Chester;Joseph, Victory;Liu, Changlu;Mani, Neelakandha S. [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 20,p. 4888 - 4891] Location in patent:supporting information