lepenine

Base Information

• Chemical Name: lepenine
• CAS No.: 111524-32-4
• Molecular Formula: C₂₂H₃₃NO₃
• Molecular Weight: 359.509
• Mol file: 111524-32-4.mol

Synonyms:7,20-Cycloatidane-1,11,15-triol,16,17-didehydro-21-ethyl-4-methyl-, (1a,11b,15b)-;8,10a-Ethano-11,3,6a-ethanylylidene-8H-indeno[2,1-b]azocine-6,7,10-triol,1-ethyldodecahydro-3-methyl-9-methylene-, [3R-(3a,6b,6aa,6ba,7a,8b,10a,10ab,11a,11ab,13R*)]-; Lepenine

Chemical Property of lepenine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 537.8°Cat760mmHg
• Flash Point: 284.2°C
• PSA: 0.00000
• Density: 1.29g/cm³
• LogP: 0.00000

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of lepenine

There total 27 articles about lepenine 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: 93.0%

(3R,6S,6aR,6bR,7S,8R,10R,10aS,11R,11aR,13R)-6-((tert-butyldimethylsilyl)oxy)-1-ethyl-3-methyl-9-methylenedodecahydro-1H-3,6a,11-(epiethane[1,1,2]triyl)-8,10a-ethanoindeno[2,1-b]azocine-7,10-diol (1603967-84-5) → lepenine (111524-32-4)

Guidance literature:

(3R,6S,6aR,6bR,7S,8R,10R,10aS,11R,11aR,13R)-6-((tert-butyldimethylsilyl)oxy)-1-ethyl-3-methyl-9-methylenedodecahydro-1H-3,6a,11-(epiethane[1,1,2]triyl)-8,10a-ethanoindeno[2,1-b]azocine-7,10-diol; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 65 ℃; for 5h;

With water; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ja503023h

Reference yield:

(R)-(7-methoxy-8-((methylsulfonyl)oxy)-4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)methyl pivalate (1603967-31-2) → lepenine (111524-32-4)

Guidance literature:

Multi-step reaction with 21 steps

1.1: tetrahydrofuran / 0.5 h / -40 °C

2.1: silver trifluoromethanesulfonate / toluene / 1 h / Reflux

3.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.33 h / 0 °C

4.1: dicyclohexyl-carbodiimide / dichloromethane / 0.05 h / 20 °C

4.2: 2 h

4.3: 0.5 h

5.1: 2,6-di-tert-butyl-4-methyl-phenol / benzonitrile / 6 h / 160 °C

6.1: borane-THF / tetrahydrofuran / 0.33 h / 20 °C

6.2: 0.02 h / 0 °C

6.3: 0.75 h

7.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.73 h / -40 °C

8.1: triethylamine; acetic acid / acetonitrile / 0.33 h / 20 °C

8.2: 1.83 h

9.1: Dess-Martin periodane / dichloromethane / 13 h / 20 °C

10.1: acetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane / 20 h / Reflux

11.1: methanol; potassium hydroxide / 3 h / 60 °C

11.2: 0.17 h / 0 °C

12.1: hydrogenchloride; methyl red; acetyl chloride; [bis(acetoxy)iodo]benzene / water / 0.17 h / 0 °C

13.1: dichloromethane / 120 h / 70 °C / 52505.3 Torr

14.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 20 °C

15.1: methanol; samarium diiodide / tetrahydrofuran / 0.07 h / 0 °C

16.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.17 h / 0 °C

17.1: borane-THF / tetrahydrofuran / 1 h / 20 °C

17.2: 0.07 h / 0 °C

17.3: 12 h / 0 - 20 °C

18.1: trifluoroacetic acid; Dess-Martin periodane / dichloromethane / 16 h / 20 °C

19.1: formic acid ethyl ester; potassium hexamethylsilazane / toluene / 16 h / 70 °C

19.2: 4 h / 50 °C

20.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.08 h / 0 °C

21.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 65 °C

With 2,6-dimethylpyridine; hydrogenchloride; methanol; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; samarium diiodide; borane-THF; methyl red; [bis(acetoxy)iodo]benzene; cerium(III) chloride heptahydrate; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; acetyl chloride; dicyclohexyl-carbodiimide; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; potassium hydroxide; formic acid ethyl ester; In tetrahydrofuran; methanol; hexane; dichloromethane; water; benzonitrile; toluene; acetonitrile; 5.1: |Diels-Alder Cycloaddition / 13.1: |Diels-Alder Cycloaddition / 20.1: |Luche Cerium Reduction;

DOI:10.1021/ja503023h

Reference yield:

((1R)-4-hydroxy-7-methoxy-8-((methylsulfonyl)oxy)-4-vinyl-1,2,3,4-tetrahydronaphthalen-1-yl)methyl pivalate (1603967-78-7) → lepenine (111524-32-4)

Guidance literature:

Multi-step reaction with 20 steps

1.1: silver trifluoromethanesulfonate / toluene / 1 h / Reflux

2.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.33 h / 0 °C

3.1: dicyclohexyl-carbodiimide / dichloromethane / 0.05 h / 20 °C

3.2: 2 h

3.3: 0.5 h

4.1: 2,6-di-tert-butyl-4-methyl-phenol / benzonitrile / 6 h / 160 °C

5.1: borane-THF / tetrahydrofuran / 0.33 h / 20 °C

5.2: 0.02 h / 0 °C

5.3: 0.75 h

6.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.73 h / -40 °C

7.1: triethylamine; acetic acid / acetonitrile / 0.33 h / 20 °C

7.2: 1.83 h

8.1: Dess-Martin periodane / dichloromethane / 13 h / 20 °C

9.1: acetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane / 20 h / Reflux

10.1: methanol; potassium hydroxide / 3 h / 60 °C

10.2: 0.17 h / 0 °C

11.1: hydrogenchloride; methyl red; acetyl chloride; [bis(acetoxy)iodo]benzene / water / 0.17 h / 0 °C

12.1: dichloromethane / 120 h / 70 °C / 52505.3 Torr

13.1: 2,6-dimethylpyridine / dichloromethane / 0.17 h / 20 °C

14.1: methanol; samarium diiodide / tetrahydrofuran / 0.07 h / 0 °C

15.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 0.17 h / 0 °C

16.1: borane-THF / tetrahydrofuran / 1 h / 20 °C

16.2: 0.07 h / 0 °C

16.3: 12 h / 0 - 20 °C

17.1: trifluoroacetic acid; Dess-Martin periodane / dichloromethane / 16 h / 20 °C

18.1: formic acid ethyl ester; potassium hexamethylsilazane / toluene / 16 h / 70 °C

18.2: 4 h / 50 °C

19.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.08 h / 0 °C

20.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 65 °C

With 2,6-dimethylpyridine; hydrogenchloride; methanol; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; samarium diiodide; borane-THF; methyl red; [bis(acetoxy)iodo]benzene; cerium(III) chloride heptahydrate; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; acetyl chloride; dicyclohexyl-carbodiimide; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; potassium hydroxide; formic acid ethyl ester; In tetrahydrofuran; methanol; hexane; dichloromethane; water; benzonitrile; toluene; acetonitrile; 4.1: |Diels-Alder Cycloaddition / 12.1: |Diels-Alder Cycloaddition / 19.1: |Luche Cerium Reduction;

DOI:10.1021/ja503023h

upstream raw materials:

(R)-(7-methoxy-8-((methylsulfonyl)oxy)-4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)methyl pivalate

((1R)-4-hydroxy-7-methoxy-8-((methylsulfonyl)oxy)-4-vinyl-1,2,3,4-tetrahydronaphthalen-1-yl)methyl pivalate

(R)-(7-methoxy-8-((methylsulfonyl)oxy)-4-vinyl-1,2-dihydronaphthalen-1-yl)methyl pivalate

(R)-(7-methoxy-8-((methylsulfonyl)oxy)-4-vinyl-1,2-dihydronaphthalen-1-yl)methanol

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