17-Hydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione 21-(ethylcarbonate)

Base Information

• Chemical Name: 17-Hydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione 21-(ethylcarbonate)
• CAS No.: 56665-79-3
• Molecular Formula: C25H32 O6
• Molecular Weight: 428.525
• European Community (EC) Number: 260-321-9
• DSSTox Substance ID: DTXSID70972109
• Nikkaji Number: J267.074G
• Wikidata: Q82955824
• Mol file: 56665-79-3.mol

Synonyms:56665-79-3;EINECS 260-321-9;17-Hydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione 21-(ethylcarbonate);DTXSID70972109;16beta-Methyl-17-hydroxy-21-(ethoxycarbonyloxy)pregna-1,4,9(11)-triene-3,20-dione;Ethyl 17-hydroxy-16-methyl-3,20-dioxopregna-1,4,9(11)-trien-21-yl carbonate;Ethyl[2-[(8S,10S,13S,14S,16S,17R)-17-hydroxy-10,13,16-trimethyl-3-oxo-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl]carbonate

Chemical Property of 17-Hydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione 21-(ethylcarbonate)

Chemical Property:

• Boiling Point: 572.9°Cat760mmHg
• Flash Point: 190.7°C
• Density: 1.23g/cm³
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 428.21988874
• Heavy Atom Count: 31
• Complexity: 913

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)OCC(=O)C1(C(CC2C1(CC=C3C2CCC4=CC(=O)C=CC43C)C)C)O
• Isomeric SMILES: CCOC(=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)C)O

Technology Process of 17-Hydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione 21-(ethylcarbonate)

There total 7 articles about 17-Hydroxy-16beta-methylpregna-1,4,9(11)-triene-3,20-dione 21-(ethylcarbonate) 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:

Carbonic acid 2-((8S,9S,10R,11R,13S,14S,16S,17R)-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester ethyl ester → 17α-hydroxy-16β-methyl-21-ethoxycarbonyloxypregna-1,4,9(11)-triene-3,20-dione (56665-79-3)

Guidance literature:

With phosphorus pentachloride; In tetrahydrofuran; at -85 ℃; for 1h; Reagent/catalyst; Solvent;

DOI:10.1021/op0102013

Reference yield:

Carbonic acid 2-((8S,9S,10R,11S,13S,14S,16S,17R)-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester ethyl ester → 17α-hydroxy-16β-methyl-21-ethoxycarbonyloxypregna-1,4,9(11)-triene-3,20-dione (56665-79-3) + Carbonic acid ethyl ester 2-((8S,9S,10R,13S,14S,16S,17R)-17-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester

Guidance literature:

With phosphorus pentachloride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(01)00274-X

Reference yield:

16β-methyl-11β,17,α21-trihydroxypregna-1,4-diene-3,20-dione → 17α-hydroxy-16β-methyl-21-ethoxycarbonyloxypregna-1,4,9(11)-triene-3,20-dione (56665-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 1 h / -15 °C

2: phosphorus pentachloride / tetrahydrofuran / 1 h / -85 °C

With phosphorus pentachloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/op0102013

upstream raw materials:

C₂₆H₃₆O₉S

Downstream raw materials:

17α,21-dihydroxy-16β-methylpregna-1,4,9(11)-triene-3,20-dione

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

16β-methyl-3,20-dioxo-1α-phenyltrithiopregna-4,9(11)diene-17α,21-diol 21-(ethylcarbonate)

Refernces

• 1、 Fu, Xiaoyong,Tann, Chou-Hong,Thiruvengadam. "Process improvements in the synthesis of corticosteroid 9,11β-epoxides". . p. 376 - 382. Retrieved 2013/09/07.