17,21-Dihydroxypregn-4-ene-3,20-dione 17,21-di(acetate)

Base Information

• Chemical Name: 17,21-Dihydroxypregn-4-ene-3,20-dione 17,21-di(acetate)
• CAS No.: 1807-15-4
• Molecular Formula: C25H34 O6
• Molecular Weight: 430.541
• European Community (EC) Number: 217-307-2
• NSC Number: 15482
• DSSTox Substance ID: DTXSID101267698
• Nikkaji Number: J199.631B
• Mol file: 1807-15-4.mol

Synonyms:1807-15-4;17,21-Dihydroxypregn-4-ene-3,20-dione 17,21-di(acetate);17,21-Diacetoxyprogesterone;EINECS 217-307-2;NSC 15482;BRN 2193141;[2-[(8R,9S,10R,13S,14S,17R)-17-acetyloxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;17,21-Dihydroxypregn-4-ene-3,20-dione diacetate;Pregn-4-ene-3,20-dione, 17,21-dihydroxy-, diacetate;4-08-00-02914 (Beilstein Handbook Reference);NSC15482;SCHEMBL835740;DTXSID101267698;NSC-15482;AKOS015955649;SS-5106;2-((8R,9S,10R,13S,14S,17R)-17-acetoxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate;17,21-diacetoxy-4-pregnene-3,20-dione;17,21-Diacetoxypregna-4-ene-3,20-dione;LS-118652;17alpha,21-diacetoxy-4-pregnene-3,20-dione;17,21-Bis(acetyloxy)pregn-4-ene-3,20-dione;W-109712;17,21-DiOHpregn-4-ene-3,20-dione-17,21-di(acetate);2-[(1S,2R,10R,11S,14R,15S)-14-(Acetyloxy)-2,15-dimethyl-5-oxotetracyclo-[8.7.0.0(2),{.0(1)(1),(1)}]heptadec-6-en-14-yl]-2-oxoethyl acetate;2-[(1S,2R,10R,11S,14R,15S)-14-(ACETYLOXY)-2,15-DIMETHYL-5-OXOTETRACYCLO[8.7.0.0(2),?.0(1)(1),(1)?]HEPTADEC-6-EN-14-YL]-2-OXOETHYL ACETATE;2-[(1S,2R,10R,11S,14R,15S)-14-(Acetyloxy)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadec-6-en-14-yl]-2-oxoethyl acetate;2-[(1S,2R,10R,11S,14R,15S)-14-(Acetyloxy)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadec-6-en-14-yl]-2-oxoethylacetate

Chemical Property of 17,21-Dihydroxypregn-4-ene-3,20-dione 17,21-di(acetate)

Chemical Property:

• Vapor Pressure: 6.92E-12mmHg at 25°C
• Boiling Point: 543.8°C at 760 mmHg
• Flash Point: 232.8°C
• PSA: 86.74000
• Density: 1.19g/cm³
• LogP: 3.95240
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 430.23553880
• Heavy Atom Count: 31
• Complexity: 858

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-[(1S,2R,10R,11S,14R,15S)-14-(Acetyloxy)-2,15-dimethyl-5-oxotetracyclo-[8.7.0.0,{.0,}]heptadec-6-en-14-yl]-2-oxoethyl 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(CCC3C2CCC4=CC(=O)CCC34C)C)OC(=O)C
• Isomeric SMILES: CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)OC(=O)C

Technology Process of 17,21-Dihydroxypregn-4-ene-3,20-dione 17,21-di(acetate)

There total 13 articles about 17,21-Dihydroxypregn-4-ene-3,20-dione 17,21-di(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:

cortexolone 21-acetate (640-87-9) + acetic anhydride (108-24-7) → 17,21-diacetoxy-4-pregnene-3,20-dione (1807-15-4)

Guidance literature:

With toluene-4-sulfonic acid; acetic acid;

DOI:10.1021/ja01110a053

Reference yield:

tetrabutylammonium acetate (10534-59-5) + 21-iodo-17α-hydroxypregn-4-ene-3,20-dione 17-acetate (102752-45-4) → 17,21-diacetoxy-4-pregnene-3,20-dione (1807-15-4)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; at 20 - 25 ℃; for 24h;

DOI:10.1007/BF00959734

Reference yield:

cortexolone 21-acetate (640-87-9) + acetic anhydride (108-24-7) → 3,17α,21-triacetoixypregna-3,5-dien-20-one (54201-62-6) + 17,21-diacetoxy-4-pregnene-3,20-dione (1807-15-4)

Guidance literature:

With ammonium hydroxide; perchloric acid; Multistep reaction. Yields of byproduct given; 1.) CH₂Cl₂, -5 to -4 deg C, 20 min, 2.) pH 7, 2 h;

DOI:10.1007/BF00768389

upstream raw materials:

cortexolone 21-acetate

acetic anhydride

tetrabutylammonium acetate

21-iodo-17α-hydroxypregn-4-ene-3,20-dione 17-acetate

Downstream raw materials:

17α,21-dihydroxy-4-pregnene-3,20-dione 17-acetate

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

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

6α-Fluor-17α-hydroxy-21-acetoxy-pregnan-(4)-trion-(3,11,20)

Refernces

• 1、 Ferraboschi, Patrizia,Mieri, Maria De,Ragonesi, Laura. "Lipase-catalyzed preparation of corticosteroid 17α-esters endowed with antiandrogenic activity". . p. 4610 - 4612. Retrieved 2008.
• 2、 -. "Cyanohydrin process". . . Retrieved 2008/06/13.