16alpha,17,21-Trihydroxypregna-1,4,9(11)-triene-3,20-dione 21-acetate

Base Information

• Chemical Name: 16alpha,17,21-Trihydroxypregna-1,4,9(11)-triene-3,20-dione 21-acetate
• CAS No.: 77017-20-0
• Molecular Formula: C23H28 O6
• Molecular Weight: 400.472
• European Community (EC) Number: 278-593-2
• UNII: FWD7KH5JFZ
• DSSTox Substance ID: DTXSID90998301
• Nikkaji Number: J309.341G
• Wikidata: Q76422149
• Mol file: 77017-20-0.mol

Synonyms:77017-20-0;16alpha,17,21-Trihydroxypregna-1,4,9(11)-triene-3,20-dione 21-acetate;EINECS 278-593-2;EC 278-593-2;(16a)-21-Acetyloxy-16,17-dihydroxy-pregna-1,4,9(11)-triene-3,20-dione;(16alpha)-21-Acetyloxy-16,17-dihydroxy-pregna-1,4,9(11)-triene-3,20-dione;[2-[(8S,10S,13S,14S,16R,17S)-16,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;FWD7KH5JFZ;SCHEMBL10625127;DTXSID90998301;(16alpha)-16,17-dihydroxy-3,20-dioxopregna-1,4,9(11)-trien-21-yl acetate;NS00089925;16alpha-Hydroxy Prednisolone-9(11)-ene Acetate;16,17-Dihydroxy-3,20-dioxopregna-1,4,9(11)-trien-21-yl acetate;(16 alpha )-21-Acetyloxy-16,17-dihydroxy-pregna-1,4,9(11)-triene-3,20-dione;(16alpha)-21-(Acetyloxy)-16,17-dihydroxypregna-1,4,9(11)-triene-3,20-dione;21-Acetyloxy-16,17-dihydroxy-pregna-1,4,9(11)-triene-3,20-dione, (16alpha)-;Pregna-1,4,9(11)-triene-3,20-dione, 21-(acetyloxy)-16,17-dihydroxy-, (16alpha)-;2-((8S,10S,13S,14S,16R,17S)-16,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

Chemical Property of 16alpha,17,21-Trihydroxypregna-1,4,9(11)-triene-3,20-dione 21-acetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 213-215 °C(Solv: acetone (67-64-1); ligroine (8032-32-4))
• Boiling Point: 576.748°C at 760 mmHg
• PKA: 11.92±0.70(Predicted)
• Flash Point: 198.046°C
• PSA: 100.90000
• Density: 1.312g/cm³
• LogP: 2.04850
• Water Solubility.: 38.72mg/L at 25℃
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 400.18858861
• Heavy Atom Count: 29
• Complexity: 882

Purity/Quality:

99.9% ^*data from raw suppliers

(16α)-21-Acetyloxy-16,17-dihydroxy-pregna-1,4,9(11)-triene-3,20-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=O)C1(C(CC2C1(CC=C3C2CCC4=CC(=O)C=CC43C)C)O)O
• Isomeric SMILES: CC(=O)OCC(=O)[C@]1([C@@H](C[C@@H]2[C@@]1(CC=C3[C@H]2CCC4=CC(=O)C=C[C@@]43C)C)O)O

Technology Process of 16alpha,17,21-Trihydroxypregna-1,4,9(11)-triene-3,20-dione 21-acetate

There total 3 articles about 16alpha,17,21-Trihydroxypregna-1,4,9(11)-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: 100.0%

2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (37413-91-5) → 16α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione-21-acetate (77017-20-0)

Guidance literature:

2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate; With formic acid; In acetone; at 0 ℃; for 0.25h;

With potassium permanganate; In acetone; at -5 - 5 ℃; for 1.5h; Temperature;

Reference yield: 92.2%

2-((10S,13S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (37413-91-5) → 16α,17α,21-trihydroxypregna-1,4,9(11)-triene-3,20-dione-21-acetate (77017-20-0)

Guidance literature:

With potassium permanganate; formic acid; In water; acetone; at 20 ℃; for 1h; Large scale;

Reference yield:

→ Acetic acid 2-((10S,13S,16R,17S)-16,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester (77017-20-0)

Guidance literature:

V, KMnO4;

upstream raw materials:

2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

2-((10S,13S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

Downstream raw materials:

(22S)-Budesonide

desisobutyryl ciclesonide

ciclesonide

desonide