A Facile Synthesis of 3β,25-dihydroxy-5α-Cholest-7-ene, the Precursor to HMG-CoA Reductase Inhibitor

Autor:	Can Jin, Bin Sun, Tengwei Xu, Zhibing Liao
Rok vydání:	2018
Předmět:	biology 010405 organic chemistry Stereochemistry Chemistry Yield (chemistry) HMG-CoA reductase 3 hydroxy 3 methylglutaryl coenzyme a reductase biology.protein General Chemistry 010402 general chemistry 01 natural sciences Ene reaction 0104 chemical sciences
Zdroj:	Journal of Chemical Research. 42:156-159
ISSN:	2047-6507 1747-5198
DOI:	10.3184/174751918x15220628915420
Popis:	An efficient four-step procedure is described for the synthesis of 3β,25-dihydroxy-5α-cholest-7-ene from 3β-hydroxy-5α-cholesta-7,24-diene in an overall yield of 34%. This product can serve as a precursor for the synthesis of an inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase. The 3β-toluene- p-sulfonate ester of 5α-cholesta-7,24-diene was obtained from natural lanolin followed by treatment with toluene- p-sulfonyl chloride. The key step in the synthesis is a very mild method for the hydroxybromination of this ester with N-bromosuccinimide in water, followed by reduction with LiAlH4to obtain the 3β-toluene- p-sulfonate ester of 25-hydroxy-5α-cholesta-7-ene. The final product was obtained after desulfonation of 3β-toluene- p-sulfonyoxy-25-hydroxy-5α-cholesta-7-ene to afford 3β,25-dihydroxy-5α-cholest-7-ene in excellent yield. The reagents are all relatively cheap, non-toxic and stable.
Databáze:	OpenAIRE
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