12aα-hydroxydeguelin

Base Information

• Chemical Name: 12aα-hydroxydeguelin
• CAS No.: 207597-97-5
• Molecular Formula: C₂₃H₂₂O₇
• Molecular Weight: 410.423
• Mol file: 207597-97-5.mol

Synonyms:

Chemical Property of 12aα-hydroxydeguelin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 12aα-hydroxydeguelin

There total 15 articles about 12aα-hydroxydeguelin 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: 44.0%

(-)-deguelin (522-17-8,54324-46-8,110508-99-1,123000-18-0) → 12aα-hydroxydeguelin (207597-97-5) + tephrosin (76-80-2)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 60 - 80 ℃; for 20h; Inert atmosphere;

DOI:10.1055/s-0037-1611654

Reference yield:

3-fluorophenol (372-20-3) → 12aα-hydroxydeguelin (207597-97-5) + tephrosin (76-80-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: hydrogenchloride / water / 1 h / -35 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / ethanol / 3 h / 60 °C / Inert atmosphere

4.1: palladium dichloride; copper dichloride / ethanol / 6 h / 60 °C

5.1: sec.-butyllithium; N,N,N,N,-tetramethylethylenediamine / cyclohexane; diethyl ether / 1 h / -78 °C / Inert atmosphere

5.2: 1 h / -78 - -50 °C / Inert atmosphere

6.1: boron trifluoride diethyl etherate / dichloromethane / -15 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

8.1: pyridinium p-toluenesulfonate / dichloromethane / 3.5 h / 20 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

10.1: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; tricyclohexylphosphine / toluene / Inert atmosphere; Reflux

11.1: diisobutylaluminium hydride / ⁽²⁾H₈-toluene / 1 h / 0 °C / Inert atmosphere

12.1: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 80 °C / Inert atmosphere

13.1: 2,6-di-tert-butyl-pyridine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane; water / 1 h / 50 °C / Inert atmosphere

14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 6.5 h / 20 °C / Inert atmosphere

15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 h / 60 - 80 °C / Inert atmosphere

With hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; n-butyllithium; 2,6-di-tert-butyl-pyridine; 15-crown-5; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; sec.-butyllithium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper dichloride; palladium dichloride; tricyclohexylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; hexane; dichloromethane; cyclohexane; ⁽²⁾H₈-toluene; water; dimethyl sulfoxide; toluene;

DOI:10.1055/s-0037-1611654

Reference yield:

2-(3-fluorophenoxy)tetrahydro-2H-pyran (185913-28-4) → 12aα-hydroxydeguelin (207597-97-5) + tephrosin (76-80-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / ethanol / 3 h / 60 °C / Inert atmosphere

3.1: palladium dichloride; copper dichloride / ethanol / 6 h / 60 °C

4.1: sec.-butyllithium; N,N,N,N,-tetramethylethylenediamine / cyclohexane; diethyl ether / 1 h / -78 °C / Inert atmosphere

4.2: 1 h / -78 - -50 °C / Inert atmosphere

5.1: boron trifluoride diethyl etherate / dichloromethane / -15 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

7.1: pyridinium p-toluenesulfonate / dichloromethane / 3.5 h / 20 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

9.1: potassium tert-butylate; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; tricyclohexylphosphine / toluene / Inert atmosphere; Reflux

10.1: diisobutylaluminium hydride / ⁽²⁾H₈-toluene / 1 h / 0 °C / Inert atmosphere

11.1: sodium hydride; 15-crown-5; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / toluene / 80 °C / Inert atmosphere

12.1: 2,6-di-tert-butyl-pyridine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane; water / 1 h / 50 °C / Inert atmosphere

13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 6.5 h / 20 °C / Inert atmosphere

14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 h / 60 - 80 °C / Inert atmosphere

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; n-butyllithium; 2,6-di-tert-butyl-pyridine; 15-crown-5; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; sec.-butyllithium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper dichloride; palladium dichloride; tricyclohexylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; hexane; dichloromethane; cyclohexane; ⁽²⁾H₈-toluene; water; dimethyl sulfoxide; toluene;

DOI:10.1055/s-0037-1611654

upstream raw materials:

3-fluorophenol

2-(3-fluorophenoxy)tetrahydro-2H-pyran