34184-82-2Relevant articles and documents
Synthesis of 17α-Hydroxy-20-oxo-pregnanes from 17(20)-Dehydro-23,24-dinorcholan-22-oic Acids
Toro, Andras,Ambrus, Gabor
, p. 5265 - 5266 (1992)
Title transformation involving catalytic epoxidation, Curtius rearrangement and acidic hydrolysis has been accomplished.This synthetic sequence offers a novel route from a partial microbial side chain degradation product of natural sterols into useful precursors of antiinflammatory, antiandrogen and gestagen pharmaceuticals.
An efficient procedure for the synthesis of 21-acetoxypregna-1,4,9(11),16-tetraene-3,20-dione
Huy, Luu D.,Diep, Nguyen T.,Vu, Tran K.,Savinova, Tatiana S.,Donova, Marina V.
, p. 225 - 231 (2020/04/27)
Background: Halogenated corticosteroids are widely used in medicine, and the global need of these steroidal APIs is estimated to be 40 - 70 tons, annually. Vietnam currently imports the pharmaceutical compounds up to 90%, in particular 100% of steroidal drugs. Currently, industrial production is based on the chemical syntheses of corticosteroids from either 16-dehydropregnenolone acetate (obtained from diosgenin) or androstenedione (obtained from phytosterol). The development of shorter synthetic schemes and more economically feasible technologies is of great significance. Introduction of 1(2)-double bond at the final stages of the corticosteroids synthesis results inpoor yield. 21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione (tetraene acetate) is a key intermediate in the synthesis of highly active halogenated corticosteroids such as dexamethasone and other halogenated corticosteroids. 21-acetoxypregna-1,4,9(11),16-tetraene-3,20-dione is a key intermediate in the synthesis of dexamethasone from the readily available and cheap 9α-hydroxyandrost-4-ene-3,17-dione. Objective: The purpose of this study was the development of an efficient and shorter procedure for the synthesis of 21-acetoxypregna-1,4,9(11),16-tetraene-3,20-dione from 9α-hydroxyan-drostenedione, which is a product of a bio-oxidative degradation of the side chain of phytosterols. Methods: Pregnane side chain was constructed using cyanohydrin method. For 1(2)-dehydrogenation, selene dioxide was applied for the introduction of Δ1(2)-double bond. Other stages of the synthesis were epimerization, Stork’s iodination procedure and dehydration. Result: 21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione was prepared from 9α-hydroxyandrostenedione in yield more than 46%. Conclusion: An efficient and practically feasible procedure for the synthesis of 21-acetoxypregna-1,4,9(11),16-tetraene-3,20-dione from 9α-hydroxyandrostenedione, a key intermediate for the synthesis of 9-haloidated corticoids, has been developed. The procedure can be applied for the production of value-added 9-haloidated corticoids.
Fluorometholone, fluorometholone acetate, and preparation method thereof
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Paragraph 0040-0042; 0051-0053; 0060-0062, (2020/03/12)
The invention discloses fluorometholone, fluorometholone acetate, and a preparation method thereof. According to the preparation method, a compound represented by a formula (II) is taken as a raw material, the compound carries out de-chlorination reaction, esterification reaction, methenylation reaction, hydrogenation reaction, fermentation de-hydrogenation reaction, epoxidation reaction, and ring-opening reaction in sequence to obtain derivatives of fluorometholone; and fluorometholone derivatives carry out hydrolysis to obtain fluorometholone. The preparation method has the advantages of short synthesis route, high yield, low raw material cost, easily available raw materials, simple and convenient purification, high product purity, and strong technological operability, is suitable for industrial production, and has a high industrialization value.
