2394-23-2

Usage

InChI:InChI=1/C21H30O4/c1-20-8-7-17-15(16(20)4-5-18(20)19(25)11-22)3-2-13-10-14(24)6-9-21(13,17)12-23/h10,15-18,22-23H,2-9,11-12H2,1H3/t15-,16-,17-,18+,20-,21+/m0/s1

Upstream product

• 57-83-0 progesterone 
• 64-85-7 21-Hydroxyprogesterone 
• 510-65-6 19-hydroxycortodoxone 
• 6901-40-2 19,21-dihydroxypregn-4-ene-3,20-dione 21-acetate 
• 145-13-1 Pregnenolone 
• 596-63-4 19-Hydroxyprogesterone 
• 104494-77-1 Acetic acid 2-methoxy-2-[(8S,9S,10S,13S,14S)-13-methyl-3-oxo-10-(tetrahydro-pyran-2-yloxymethyl)-1,2,3,6,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-(17Z)-ylidene]-ethyl ester 
• 1778-02-5 Pregnenolone acetate 
• 2723-07-1 5-Bromo-6β-hydroxy-20-oxo-5α-pregnan-3β-yl acetate 
• 41767-48-0 5-Bromo-20-oxo-6β,19-epoxy-5α-pregnan-3β-yl acetate 
• 90075-56-2 5-bromo-3β,21-dihydroxy-6β,19-epoxy-5α-pregnan-20-one 21-acetate 
• 90095-34-4 5-Bromo-3,20-dioxo-6β,19-epoxy-5α-pregnan-21-yl acetate 
• 7090-07-5 3,20-Dioxo-6β,19-epoxypregn-4-en-21-yl acetate 
• 5563-20-2 3β-hydroxy-5-bromo-6β,19-epoxy-5α-pregnan-20-one 

Downstream Products

• 116928-58-6 19,21-bis-benzoyloxy-11β-hydroxy-pregn-4-ene-3,20-dione 

Relevant academic research and scientific papers

A biocatalytic hydroxylation-enabled unified approach to C19-hydroxylated steroids

Steroidal C19-hydroxylation is pivotal to the synthesis of naturally occurring bioactive C19-OH steroids and 19-norsteroidal pharmaceuticals. However, realizing this transformation is proved to be challenging through either chemical or biological synthesis. Herein, we report a highly efficient method to synthesize 19-OH-cortexolone in 80% efficiency at the multi-gram scale. The obtained C19-OH-cortexolone can be readily transformed to various synthetically useful intermediates including the industrially valuable 19-OH-androstenedione, which can serve as a basis for synthesis of C19-functionalized steroids as well as 19-nor steroidal drugs. Using this biocatalytic C19-hydroxylation method, the unified synthesis of six C19-hydroxylated pregnanes is achieved in just 4 to 9 steps. In addition, the structure of sclerosteroid B is revised on the basis of our synthesis.

19 Hydroxylated cortisone derivative and preparation method 19 - hydroxyl androstenedione (by machine translation)

The invention discloses 19 hydroxylated cortisone derivatives and a preparation method, namely 19 - hydroxyandrostenedione. Belong to organic synthesis and pharmacy field. To the invention, 19 - hydroxyl group can be used as a raw material, 19 - hydroxyl can be supported in a plurality of groups under the action of hydrogen peroxide, trimethyl iodosilane, palladium carbon, dichloro dicyanobenzene quinone, iodobenzene, sodium borohydride, sodium periodate and the like respectively. 19 - hydroxyl can be supported to 19 - respectively. B ring can be supported by structural modification 17. 21 And/or 19-position hydroxyl groups are substituted; cleavage 19 - hydroxyl groups may support many loose side chains. The preparation method of the essential intermediate 19 - hydroxyandrostenedione synthesized by the norethindrone contraceptive is greatly improved, and the drug production cost. (by machine translation)

New Syntheses of 19,21-Dihydropregn-4-ene-3,20-dione, 21-Hydroxy-19-norpregn-4-ene-3,20-dione, and 11β,19,21-trihydroxypregn-4-ene-3,20-dione

19,21-Dihydroxypregn-4-ene-3,20-dione has been synthesized from 3β-acetoxypregn-5-en-20-one via the "hypoiodite reaction" , and Henbest acetoxylation at C-21; oxidation of the intermediate 21-monoacetate to 19-oxo derivative and alkaline cleavage gave 21-hydroxy-19-norpregn-4-ene-3,20-dione.A similar synthesis of 11β,19,21-trihydroxypregn-4-ene-3,20-dione from 3β-acetoxypregn-5-ene-11,20-dione proceeded through intermediates with the 11β-hydroxy function protected as its acetate.Unusual features mainly of conformational origin were observed in the presence of the 11β-acetoxy substituent; some were helpful to the synthesis, while others led to undesirable side reactions.