6alpha,9-Difluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate

Base Information

• Chemical Name: 6alpha,9-Difluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate
• CAS No.: 52-70-0
• Molecular Formula: C23H28 F2 O6
• Molecular Weight: 438.469
• European Community (EC) Number: 200-150-9
• UNII: 953PJH8Y9L
• DSSTox Substance ID: DTXSID90966323
• Nikkaji Number: J213.536A
• ChEMBL ID: CHEMBL3250151
• Mol file: 52-70-0.mol

Synonyms:52-70-0;6alpha,9-Difluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate;EINECS 200-150-9;[2-[(6S,8S,9R,10S,11S,13S,14S,17R)-6,9-difluoro-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;(6alpha,11beta)-21-(Acetyloxy)-6,9-difluoro-11,17-dihydroxypregna-1,4-diene-3,20-dione;Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-6,9-difluoro-11,17-dihydroxy-, (6alpha,11beta)-;Pregna-1,4-diene-3,20-dione, 6alpha,9-difluoro-11beta,17,21-trihydroxy-, 21-acetate;(6|A,11|A)-21-(Acetyloxy)-6,9-difluoro-11,17-dihydroxypregna-1,4-diene-3,20-dione;6alpha,9alpha-Difluoroprednisolone 21-acetate;953PJH8Y9L;CHEMBL3250151;SCHEMBL15501297;DTXSID90966323;C23H28F2O6;C23-H28-F2-O6;C15920;6,9-Difluoro-11,17-dihydroxy-3,20-dioxopregna-1,4-dien-21-yl acetate;21-(Acetyloxy)-6alpha,9-difluoro-11beta,17-dihydroxypregna-1,4-diene-3,20-dione;6alpha,9-difluor-11beta,17,21-trihydroxypregna-1,4-dien-3,20-dion-21-acetat;(6A,11BETA)-21-(ACETYLOXY)-6,9-DIFLUORO-11,17-DIHYDROXYPREGNA-1,4-DIENE-3,20-DIONE

Chemical Property of 6alpha,9-Difluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate

Chemical Property:

• Vapor Pressure: 8.98E-16mmHg at 25°C
• Boiling Point: 578.1°Cat760mmHg
• Flash Point: 303.4°C
• PSA: 100.90000
• Density: 1.35g/cm³
• LogP: 2.16850
• Storage Temp.: Refrigerator
• Solubility.: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 438.18539493
• Heavy Atom Count: 31
• Complexity: 914

Purity/Quality:

99%, ^*data from raw suppliers

6α,?9α-?Difluoroprednisolone21-Acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=O)C1(CCC2C1(CC(C3(C2CC(C4=CC(=O)C=CC43C)F)F)O)C)O
• Isomeric SMILES: CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2C[C@@H](C4=CC(=O)C=C[C@@]43C)F)F)O)C)O
• Uses: 6α,9α-?Difluoroprednisolone 21-Acetate, is an impurity of Difluprednate (D445925), which is shown to have antiinflammatory activity.

Technology Process of 6alpha,9-Difluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate

There total 19 articles about 6alpha,9-Difluoro-11beta,17,21-trihydroxypregna-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:

21-acetyloxy-9β,11β-epoxy-6α-fluoro-17α-hydroxy-1,4-diene-3,20-dione (3802-45-7) → 21-acetoxy-6α,9-difluoro-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione (52-70-0)

Guidance literature:

With hydrogen fluoride; tert-butylhydroquinone; In dichloromethane; at -10 - -5 ℃; for 2h; Solvent; Reagent/catalyst;

Reference yield:

pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (4380-55-6) → 21-acetoxy-6α,9-difluoro-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione (52-70-0)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrafluoroboric acid; 5,5-dibromohydantoin / acetone; water / 0 - 5 °C

2: potassium carbonate / acetone; water / 16 h / 25 - 40 °C

3: pyridine / acetonitrile / 4 h / 82 - 84 °C / Inert atmosphere

4: Selectfluor / acetonitrile / -20 - -12 °C

5: hydrogen fluoride; tert-butylhydroquinone / dichloromethane / 2 h / -10 - -5 °C

With pyridine; tetrafluoroboric acid; 5,5-dibromohydantoin; hydrogen fluoride; potassium carbonate; Selectfluor; tert-butylhydroquinone; In dichloromethane; water; acetone; acetonitrile;

Reference yield:

21-acetoxy-9-bromo-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione (4224-31-1) → 21-acetoxy-6α,9-difluoro-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione (52-70-0)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / acetone; water / 16 h / 25 - 40 °C

2: pyridine / acetonitrile / 4 h / 82 - 84 °C / Inert atmosphere

3: Selectfluor / acetonitrile / -20 - -12 °C

4: hydrogen fluoride; tert-butylhydroquinone / dichloromethane / 2 h / -10 - -5 °C

With pyridine; hydrogen fluoride; potassium carbonate; Selectfluor; tert-butylhydroquinone; In dichloromethane; water; acetone; acetonitrile;

upstream raw materials:

21-acetoxy-6α,9-difluoro-11β,17-dihydroxy-pregn-4-ene-3,20-dione

21-acetoxy-9,11β-epoxy-6α-fluoro-17-hydroxy-9β-pregna-1,4-diene-3,20-dione

17α,21-diacetoxy-5α,6-oxide-3,3-ethylenedioxypregnan-20-one

17,21-diacetoxy-4-pregnene-3,20-dione

Downstream raw materials:

6α,9-difluoro-11β,17,21-trihydroxy-pregna-1,4-diene-3,20-dione

Refernces