WX5VW74Skc

Base Information

• Chemical Name: WX5VW74Skc
• CAS No.: 610785-40-5
• Molecular Formula: C₂₇H₃₂O₄
• Molecular Weight: 420.549
• UNII: WX5VW74SKC
• Mol file: 610785-40-5.mol

Synonyms:WX5VW74SKC;UNII-WX5VW74SKC;610785-40-5;(7alpha,17alpha)-17-Hydroxy-7-(5-methyl-2-furanyl)-3-oxo-pregna-4,9(11)-diene-21-carboxylic acid gamma-lactone;Pregna-4,9(11)-diene-21-carboxylic acid, 17-hydroxy-7-(5-methyl-2-furanyl)-3-oxo-, gamma-lactone, (7alpha,17alpha)-;SCHEMBL14084990;(7.ALPHA.,17.ALPHA.)-17-HYDROXY-7-(5-METHYL-2-FURANYL)-3-OXO-PREGNA-4,9(11)-DIENE-21-CARBOXYLIC ACID .GAMMA.-LACTONE;PREGNA-4,9(11)-DIENE-21-CARBOXYLIC ACID, 17-HYDROXY-7-(5-METHYL-2-FURANYL)-3-OXO-, .GAMMA.-LACTONE, (7.ALPHA.,17.ALPHA.)-

Chemical Property of WX5VW74Skc

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 420.23005950
• Heavy Atom Count: 31
• Complexity: 901

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(O1)C2CC3=CC(=O)CCC3(C4=CCC5(C(C24)CCC56CCC(=O)O6)C)C
• Isomeric SMILES: CC1=CC=C(O1)[C@@H]2CC3=CC(=O)CC[C@@]3(C4=CC[C@]5([C@H]([C@H]24)CC[C@@]56CCC(=O)O6)C)C

Technology Process of WX5VW74Skc

There total 2 articles about WX5VW74Skc 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: 77.7%

2-methylfuran (534-22-5) + Δ9(11)-canrenone (95716-71-5) → 17β-hydroxy-7α-(5'-methyl-2'-furyl)-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone (610785-40-5)

Guidance literature:

With ethanol; boron trifluoride diethyl etherate; isopropyl alcohol; In acetonitrile; at -18.4 ℃; for 24h;

DOI:10.1021/ol060503v

Reference yield: 3.9%

2-methylfuran (534-22-5) + Δ9(11)-canrenone (95716-71-5) → 17β-hydroxy-7α-(5'-methyl-2'-furyl)-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone (610785-40-5) + 17β-hydroxy-7β-(5'-methyl-2'-furyl)-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone

Guidance literature:

With ethanol; boron trifluoride diethyl etherate; In nitromethane; at -18.4 ℃; for 17h;

DOI:10.1021/ol060503v

Reference yield:

17β-hydroxy-7α-(5'-methyl-2'-furyl)-pregna-4,9(11)-dien-3-one-21-carboxylic acid γ-lactone (610785-40-5) → eplerenone (107724-20-9)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate; 5,5-dibromohydantoin / tetrahydrofuran; water / 20 °C / Inert atmosphere

2: ozone / -50 °C

3: trichloroacetamide; potassium phosphate; dihydrogen peroxide / dichloromethane / 20 °C

With potassium phosphate; trichloroacetamide; 5,5-dibromohydantoin; dihydrogen peroxide; potassium carbonate; ozone; In tetrahydrofuran; dichloromethane; water;

upstream raw materials:

2-methylfuran

Δ⁹⁽¹¹⁾-canrenone

Downstream raw materials:

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

eplerenone

Refernces

• 1、 Pearlman, Bruce A.,Padilla, Amphlett G.,Hach, John T.,Havens, Jeffrey L.,Pillai, Muniraj D.. "A new approach to the furan degradation problem involving ozonolysis of the trans-enedione and its use in a cost-effective synthesis of eplerenone". . p. 2111 - 2113. Retrieved 2007/10/03.