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

Base Information

• Chemical Name: 17,21-dihydroxy-16alpha-methylpregna-1,4,9(11)-triene-3,20-dione
• CAS No.: 13209-41-1
• Deprecated CAS: 106073-65-8
• Molecular Formula: C22H28 O4
• Molecular Weight: 356.462
• European Community (EC) Number: 236-177-8
• UNII: 8XP29XMB43
• DSSTox Substance ID: DTXSID60927527
• Nikkaji Number: J213.750J
• Wikipedia: Vamorolone
• Wikidata: Q27089127
• NCI Thesaurus Code: C152825
• Metabolomics Workbench ID: 155289
• ChEMBL ID: CHEMBL2348780
• Mol file: 13209-41-1.mol

Synonyms:Pregna-1,4,9(11)-triene-3,20-dione,17,21-dihydroxy-16a-methyl- (6CI,7CI,8CI); 17a,21-Dihydroxy-16a-methylpregna-1,4,9(11)-triene-3,20-dione

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

Chemical Property:

• Vapor Pressure: 2.63E-14mmHg at 25°C
• Melting Point: 228-231 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• Boiling Point: 548.3°C at 760 mmHg
• PKA: 12.53±0.70(Predicted)
• Flash Point: 299.4°C
• PSA: 74.60000
• Density: 1.24g/cm³
• LogP: 2.75290
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Dioxane (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 356.19875937
• Heavy Atom Count: 26
• Complexity: 775

Purity/Quality:

99% ^*data from raw suppliers

16α-Methyl-9,11-dehydroPrednisolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C3=CCC2(C1(C(=O)CO)O)C)C
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4(C3=CC[C@@]2([C@]1(C(=O)CO)O)C)C
• Recent ClinicalTrials: A Study to Assess the Efficacy and Safety of Vamorolone in Boys With Duchenne Muscular Dystrophy (DMD)
• Recent EU Clinical Trials: A Phase IIb Randomized, Double-blind, Parallel Group, Placebo- and Active-controlled Study with Double-Blind Extension to Assess the Efficacy and Safety of Vamorolone in Ambulant Boys with Duchenne Muscular Dystrophy (DMD)
• Uses: A related intermediate of Prednisolone (P703740).

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

There total 9 articles about 17,21-dihydroxy-16alpha-methylpregna-1,4,9(11)-triene-3,20-dione 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: 80.0%

C25H36O4Si → (8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one (13209-41-1)

Guidance literature:

With hydrogenchloride; In pentan-1-ol;

Reference yield:

17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate (10106-41-9) → (8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one (13209-41-1)

Guidance literature:

With water; potassium carbonate; In methanol; at 0 - 20 ℃;

Reference yield:

C25H36O2Si → (8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one (13209-41-1)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C

2: hydrogenchloride / pentan-1-ol

With hydrogenchloride; potassium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; pentan-1-ol;

upstream raw materials:

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

2-((10S,13S,16R,17R)-17-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

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

17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate

Downstream raw materials:

dexamethasone

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

Refernces

• 1、 -. "AQUEOUS ORAL PHARMACEUTICAL SUSPENSION COMPOSITIONS". . . Retrieved 2020/09/22.
• 2、 -. "A 17, 21 - double-hydroxy steroid derivatives". . . Retrieved 2018/04/02.