Cholesteryl hemisuccinate synthesis
- Product Name:Cholesteryl hemisuccinate
- CAS Number:1510-21-0
- Molecular formula:C31H50O4
- Molecular Weight:486.73
108-30-5
57-88-5
1510-21-0
GENERAL METHOD: Succinic anhydride (14.7 mmol, 1.57 eq.) and 4-dimethylaminopyridine (DMAP, 1.584 mmol, 0.17 eq.) were sequentially added to a solution of (3β)-cholest-5-en-3-ol (9.37 mmol) in pyridine (28 mL). The reaction mixture was stirred at room temperature for 7 days. Upon completion of the reaction, the mixture was poured into ice water and the pH was adjusted to 7 with dilute hydrochloric acid and subsequently extracted with chloroform. The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography to afford the target compounds in 79% or 96% yield and >99.9% analytical purity (see Scheme 1-2). Analytical data for compounds 2 and 12 are detailed in the Supplementary Material.
Yield:1510-21-0 96%
Reaction Conditions:
with pyridine;dmap at 20; for 168 h;
Steps:
2.2 Synthetic protocol I: 4-[(3β)-lanosta-8,24-dien-3-yloxy]-4-oxobutanoic acid (2) and 4-[(3β)-cholest-5-en-3-yloxy]-4-oxobutanoic acid (12)
General procedure: Succinic anhydride (14.7mmol; 1.57equiv) and DMAP (1.584mmol, 0.17equiv) was added to a solution of (3β)-lanosta-8,24-dien-3-ol (1) or (3β)-cholest-5-en-3-ol (11) (9.37mmol) in pyridine (28mL). The reaction mixture was stirred over 7days at r.t. After stopping the reaction, the resulting mixture was poured onto ice, and hydrochloric acid was added to adjust pH=7, extracted with chloroform, and dried over sodium sulfate. Evaporation of the solvent gave a solid which was purified by column chromatography, affording the products (2) or (12) in 79% or 96% yield, respectively, and with >99.9% analytical purity (Schemes 1-2). The analytical data of the products 2 and 12 are presented in the Supplementary material.
References:
Bildziukevich, Uladzimir;Rárová, Lucie;?aman, David;Havlí?ek, Libor;Dra?ar, Pavel;Wimmer, Zdeněk [Steroids,2013,vol. 78,# 14,p. 1347 - 1352]
57-88-5
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1510-21-0
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$35.00/1g
57-88-5
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$10.00/1g
543-20-4
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1510-21-0
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1510-20-9
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