9beta,11beta-Epoxy-6alpha-fluoro-17,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 21-acetate

Base Information

• Chemical Name: 9beta,11beta-Epoxy-6alpha-fluoro-17,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 21-acetate
• CAS No.: 4571-51-1
• Molecular Formula: C24H29FO6
• Molecular Weight: 432.489
• European Community (EC) Number: 224-953-9
• DSSTox Substance ID: DTXSID10963430
• Nikkaji Number: J297.826A
• Wikidata: Q76009930
• Mol file: 4571-51-1.mol

Synonyms:4571-51-1;EINECS 224-953-9;9beta,11beta-Epoxy-6alpha-fluoro-17,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 21-acetate;[2-[(1S,2S,8S,10S,11S,13R,14R,15S,17S)-8-Fluoro-14-hydroxy-2,13,15-trimethyl-5-oxo-18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadeca-3,6-dien-14-yl]-2-oxoethyl] acetate;SCHEMBL11443532;DTXSID10963430;AKOS030254948;6-Fluoro-17-hydroxy-16-methyl-3,20-dioxo-9,11-epoxypregna-1,4-dien-21-yl acetate;Acetic acid 9beta,11beta-epoxy-6alpha-fluoro-17-hydroxy-16alpha-methyl-3,20-dioxopregna-1,4-dien-21-yl ester

Chemical Property of 9beta,11beta-Epoxy-6alpha-fluoro-17,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 21-acetate

Chemical Property:

• Boiling Point: 576.8°Cat760mmHg
• Flash Point: 302.6°C
• PSA: 93.20000
• Density: 1.33g/cm³
• LogP: 2.48290
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 432.19481680
• Heavy Atom Count: 31
• Complexity: 956

Purity/Quality:

99.9% ^*data from raw suppliers

(6α,9β,11β,16α)-21-(Acetyloxy)-9,11-epoxy-6-fluoro-17-hydroxy-16-methylpregna-1,4-diene-3,20-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CC(C4=CC(=O)C=CC4(C35C(O5)CC2(C1(C(=O)COC(=O)C)O)C)C)F
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]35[C@@H](O5)C[C@@]2([C@]1(C(=O)COC(=O)C)O)C)C)F

Technology Process of 9beta,11beta-Epoxy-6alpha-fluoro-17,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 21-acetate

There total 6 articles about 9beta,11beta-Epoxy-6alpha-fluoro-17,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 21-acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

9β,11β-epoxy-3-t-butyl-dimethylsilyloxy-17α,21-dihydroxy-16α-methylpregna-1,3,5-triene-20-one 21-acetate → 9β,11-epoxy-6α-fluoro-16α-methyl-17,21-dihydroxy-1,4-diene-3,20-dione 21-acetate (4571-51-1) + 6β-fluoro-9β,11β-epoxy-17α,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate (494870-04-1)

Guidance literature:

9β,11β-epoxy-3-t-butyl-dimethylsilyloxy-17α,21-dihydroxy-16α-methylpregna-1,3,5-triene-20-one 21-acetate; With 1H-imidazole; N-fluorobis(benzenesulfon)imide; In dichloromethane; at 15 - 20 ℃; for 2h;

With water; In dichloromethane; for 0.25h;

Reference yield:

17α,21-dihydroxy-9β,11β-epoxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate (2884-51-7) → 9β,11-epoxy-6α-fluoro-16α-methyl-17,21-dihydroxy-1,4-diene-3,20-dione 21-acetate (4571-51-1)

Guidance literature:

17α,21-dihydroxy-9β,11β-epoxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate; With Isopropenyl acetate; sulfuric acid; for 0.5h;

With Selectfluor; In acetonitrile;

Reference yield:

9β,11β-epoxy-3,17α,21-trihydroxy-16α-methylpregna-1,3,5-triene-20-one 3-benzoate-21-acetate (477898-18-3) → 9β,11-epoxy-6α-fluoro-16α-methyl-17,21-dihydroxy-1,4-diene-3,20-dione 21-acetate (4571-51-1) + 6β-fluoro-9β,11β-epoxy-17α,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate (494870-04-1)

Guidance literature:

With Selectfluor; In water; acetonitrile; at 0 ℃; for 1h;

upstream raw materials:

9β,11β-epoxy-3,17α,21-trihydroxy-16α-methylpregna-1,3,5-triene-20-one 3-benzoate-21-acetate

9α-Bromo-6α-fluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate

17α,21-dihydroxy-9β,11β-epoxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate

9β,11-epoxy-16α-methyl-3,17,21-trihydroxy-1,3,5-triene-20-one 21-acetate 3-(4-nitrobenzoate)

Downstream raw materials:

6α,9-difluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione

flumetasone

epoxyparamethasone

9α-chloro-6α-fluoro-11β,21-dihydroxy-16α-methyl-1,4-pregnadiene-3,20-dione

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF 17-DESOXY-CORTICOSTEROIDS". Page/Page column 19. . Retrieved 2012/02/05.
• 2、 -. "Selective epoxidation of steroidal bromohydrins". . . Retrieved 2008/06/13.