6alpha,9-Difluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate

Base Information

• Chemical Name: 6alpha,9-Difluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate
• CAS No.: 2326-26-3
• Molecular Formula: C23H26 F2 O5
• Molecular Weight: 420.453
• European Community (EC) Number: 219-040-7
• DSSTox Substance ID: DTXSID10945953
• Nikkaji Number: J213.195A
• Wikidata: Q82923411
• Mol file: 2326-26-3.mol

Synonyms:2326-26-3;6alpha,9-Difluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate;EINECS 219-040-7;[2-[(6S,8S,9R,10S,11S,13S,14S)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-7,8,11,12,14,15-hexahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;C23H26F2O5;C23-H26-F2-O5;SCHEMBL2300385;DTXSID10945953;6,9-Difluoro-11-hydroxy-3,20-dioxopregna-1,4,16-trien-21-yl acetate;6alpha,9-Difluoro-11beta,21-dihydroxy-pregna-1,4,16-triene-3,20-dione;21-Acetyloxy-6alpha,9-difluoro-11beta-hydroxypregna-1,4,16-triene-3,20-dione;Acetic acid 2-((6S,8S,9R,10S,11S,13S,14S)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester

Chemical Property of 6alpha,9-Difluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate

Chemical Property:

• Vapor Pressure: 1.77E-14mmHg at 25°C
• Melting Point: 209-210 °C
• Boiling Point: 551.8°Cat760mmHg
• PKA: 12.81±0.70(Predicted)
• Flash Point: 287.5°C
• PSA: 80.67000
• Density: 1.32g/cm³
• LogP: 2.97370
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 420.17483025
• Heavy Atom Count: 30
• Complexity: 921

Purity/Quality:

99%, ^*data from raw 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
• Isomeric SMILES: CC(=O)OCC(=O)C1=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
• Uses: 6alpha,9-difluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate is used in the preparation of anti-inflammatory and antiallergic agents. A glucocorticoid.

Technology Process of 6alpha,9-Difluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate

There total 9 articles about 6alpha,9-Difluoro-11beta,21-dihydroxypregna-1,4,16-triene-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: 95.0%

difluprednate → acetic acid 2-((6S,8S,9R,10S,11S,13S,14S)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15-decahydro-3H-cyclopenta[a]phenanthrene-17-yl)-2-oxo-ethyl ester (2326-26-3)

Guidance literature:

With potassium acetate; In N,N-dimethyl-formamide; at 100 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b01873

Reference yield:

17α,21-diacetyloxy-11β-hydroxy-6α, 9α-difluoro-1,4-diene-3,20-dione → acetic acid 2-((6S,8S,9R,10S,11S,13S,14S)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15-decahydro-3H-cyclopenta[a]phenanthrene-17-yl)-2-oxo-ethyl ester (2326-26-3)

Guidance literature:

With potassium acetate; In N,N-dimethyl-formamide; at 90 - 100 ℃; for 8h; Inert atmosphere;

DOI:10.1246/cl.170923

Reference yield:

anecortave (7753-60-8) → acetic acid 2-((6S,8S,9R,10S,11S,13S,14S)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15-decahydro-3H-cyclopenta[a]phenanthrene-17-yl)-2-oxo-ethyl ester (2326-26-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: D-glucose / aq. phosphate buffer

2.1: perchloric acid / acetone; water / 0.17 h / 0 - 5 °C

2.2: 1 h / 0 - 5 °C

2.3: 2 h / 0 - 35 °C

3.1: pyridine; toluene-4-sulfonic acid; Isopropenyl acetate / acetonitrile; methanol / 3 h / 80 °C / Inert atmosphere

4.1: Selectfluor^TM / acetonitrile / 8.5 h

5.1: toluene-4-sulfonic acid / 12 h / 70 °C

6.1: hydrogen fluoride; N,N-dimethyl acetamide / water / -15 °C

7.1: potassium acetate / N,N-dimethyl-formamide / 8 h / 90 - 100 °C / Inert atmosphere

With pyridine; perchloric acid; Isopropenyl acetate; D-glucose; N,N-dimethyl acetamide; hydrogen fluoride; potassium acetate; toluene-4-sulfonic acid; In methanol; aq. phosphate buffer; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1246/cl.170923

upstream raw materials:

anecortave

pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate

21-acetyloxy-9β,11β-epoxy-17α-hydroxy-1,4-diene-3,20-dione

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

Downstream raw materials:

(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-8-benzyl-4b,12-difluoro-5-hydroxy-6b-(2-hydroxy-acetyl)-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-azapentaleno[2,1-a]phenanthrene-2-one

Carbonic acid 2-((4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-8-benzyl-4b,12-difluoro-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl ester ethyl ester

(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-5-hydroxy-6b-(2-hydroxy-acetyl)-4a,6a-dimethyl-2-oxo-8-phenylcarbamoyl-2,4a,4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-hexadecahydro-8-aza-pentaleno[2,1-a]phenanthrene-9-carboxylic acid ethyl ester

(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-8-Benzenesulfonyl-4b,12-difluoro-5-hydroxy-6b-(2-hydroxy-acetyl)-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-hexadecahydro-8-aza-pentaleno[2,1-a]phenanthrene-9-carboxylic acid ethyl ester

Refernces

• 1、 Ghidini, Eleonora,Marchini, Gessica,Capelli, Anna Maria,Carnini, Chiara,Cenacchi, Valentina,Fioni, Alessandro,Facchinetti, Fabrizio,Rancati, Fabio. "Novel Pyrrolidine Derivatives of Budesonide as Long Acting Inhaled Corticosteroids for the Treatment of Pulmonary Inflammatory Diseases". supporting information. p. 4757 - 4773. Retrieved 2018/05/23.
• 2、 -. "ANTI -INFLAMMATORY STEROIDS CONDENSED IN POSITION 16,17 WITH PYRROLIDINE RING". Page/Page column 20-21. . Retrieved 2013/03/26.