11,21-Dihydroxy-6-methylpregna-4,17-dien-3-one

Base Information

• Chemical Name: 11,21-Dihydroxy-6-methylpregna-4,17-dien-3-one
• CAS No.: 3386-04-7
• Molecular Formula: C₂₂H₃₂O₃
• Molecular Weight: 344.494
• European Community (EC) Number: 222-204-0
• DSSTox Substance ID: DTXSID40955449
• Mol file: 3386-04-7.mol

Synonyms:DTXSID40955449;3386-04-7;11,21-Dihydroxy-6-methylpregna-4,17-dien-3-one

Chemical Property of 11,21-Dihydroxy-6-methylpregna-4,17-dien-3-one

Chemical Property:

• Vapor Pressure: 1.29E-12mmHg at 25°C
• Boiling Point: 511.8°Cat760mmHg
• Flash Point: 277.4°C
• PSA: 57.53000
• Density: 1.16g/cm³
• LogP: 3.65380
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 344.23514488
• Heavy Atom Count: 25
• Complexity: 648

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CCC(=CCO)C3(CC(C2C4(C1=CC(=O)CC4)C)O)C
• Isomeric SMILES: C[C@H]1C[C@H]2[C@@H]3CCC(=CCO)[C@]3(C[C@@H]([C@@H]2[C@@]4(C1=CC(=O)CC4)C)O)C

Technology Process of 11,21-Dihydroxy-6-methylpregna-4,17-dien-3-one

There total 2 articles about 11,21-Dihydroxy-6-methylpregna-4,17-dien-3-one 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:

→ 11-Hydroxy-17-[2-hydroxy-eth-(E)-ylidene]-6,10,13-trimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (3386-04-7,14423-17-7)

Guidance literature:

Enaminketon, Red.;

Reference yield:

6-methyl-11-oxo-3-pyrrolidino-pregna-3,5,17(20)c-trien-21-oic acid methyl ester (1968-77-0) → 11β,21-dihydroxy-6α-methyl-pregna-4,17(20)c-dien-3-one (3386-04-7,14423-17-7)

Guidance literature:

With lithium aluminium tetrahydride; diethyl ether; Behandeln des Reaktionsprodukts mit wss.-methanol.Alkalilauge;

DOI:10.1021/ja01604a078

Reference yield:

11β,21-dihydroxy-6α-methyl-pregna-4,17(20)c-dien-3-one (3386-04-7,14423-17-7) → methylprednisolone acetate (53-36-1,1048031-82-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Dehydrierung durch Septomyxa affinis und anschliessende Acetylierung

2: diacetoxy-phenyl-iodan; OsO₄; tert-butyl alcohol / Reagens 4: Pyridin

With osmium(VIII) oxide; [bis(acetoxy)iodo]benzene; tert-butyl alcohol;

DOI:10.1021/ja01604a078

upstream raw materials:

6-methyl-11-oxo-3-pyrrolidino-pregna-3,5,17⁽²⁰⁾c-trien-21-oic acid methyl ester

Downstream raw materials:

17α,21-dihydroxy-6α-methylpregna-1,4-diene-3,11,20-trione

Methylprednisolone

methylprednisolone acetate