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Synthesis of phthalic acid esters and synthesis and characterization of 3β,5α-dihydroxy-16-pregnene-6,20-dione-3-aromatic acid ester

AddTime:2019-07-24

A new compound, 3β-hydroxypregnenone decanoate, was synthesized by epoxidation, ring-opening, hydrolysis and esterification in a 4-step reaction using 16-dehydropregnenolone acetate and citric acid as raw materials. The structure was 1H. NMR, 13C NMR, IR and MS characterization

A series of novel 3β-hydroxyl groups were synthesized by epoxidation, ring opening, hydrolysis and esterification in a four-step reaction of epoxidized, ring-opening, hydrolysis and esterification, which is an inexpensive and easily available steroidal intermediate, 16-dehydropregnenolone acetate (16-DPA)

The ketene aryl aryl ester compound was structurally characterized by 1H NMR, 13C NMR, IR, MS and LC-MS to confirm the structure of the new compound. These compounds have broad application prospects in 5α-reductase inhibitors, antiandrogen, lipid lowering and antioxidants. This thesis mainly includes the following aspects: 1. Using 16-DPA as the starting material, through C5-double bond epoxidation, ring opening, C3-acetyl hydrolysis and esterification four steps, a series of reactions were obtained. The 16-DPA derivative 3?,5a-dihydroxy-16-pregnene-6,20-dione aromatic formate having an ester group side chain at the C3 position. For the reaction of C3-acetyl hydrolysis to form 3β,5α-dihydroxy-16-pregnene-6,20-dione, by changing the hydrolysis conditions from sodium hydroxide/tert-butanol to potassium hydroxide/methanol The yield. 2. Found 3β,5α-dihydroxy-16-pregnene-6,20-dione and aromatic carboxylic acid in N,N'-dicyclohexylcarbodiimide (DCC) and p-dimethylaminopyridine ( The esterification reaction under the action of DMAP) is regioselective.

 The 5-position hydroxyl group is difficult to undergo an esterification reaction due to the steric hindrance of the 5-position hydroxyl group in the steroid substrate and the intramolecular hydrogen bond of the 5-position hydroxyl group with the adjacent carbonyl oxygen atom. The 3-position hydroxyl group is prone to esterification reaction, and the reaction yield is 44% to 98%. Email:sales@danaopharm.com;Tel:+86-719-5251167/18986895161.

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