3aβ,4,4aα,5,6,7,8,8a,9,9aβ-decahydro-3β,8aβ-dimethyl-5-methylene-3β-(phenylthio)naphtho<2,3-b>furan-2(3H)-one

Base Information

• Chemical Name: 3aβ,4,4aα,5,6,7,8,8a,9,9aβ-decahydro-3β,8aβ-dimethyl-5-methylene-3β-(phenylthio)naphtho<2,3-b>furan-2(3H)-one
• CAS No.: 74064-03-2
• Molecular Formula: C₂₁H₂₆O₂S
• Molecular Weight: 342.502
• Mol file: 74064-03-2.mol

Synonyms:

Chemical Property of 3aβ,4,4aα,5,6,7,8,8a,9,9aβ-decahydro-3β,8aβ-dimethyl-5-methylene-3β-(phenylthio)naphtho<2,3-b>furan-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3aβ,4,4aα,5,6,7,8,8a,9,9aβ-decahydro-3β,8aβ-dimethyl-5-methylene-3β-(phenylthio)naphtho<2,3-b>furan-2(3H)-one

There total 26 articles about 3aβ,4,4aα,5,6,7,8,8a,9,9aβ-decahydro-3β,8aβ-dimethyl-5-methylene-3β-(phenylthio)naphtho<2,3-b>furan-2(3H)-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:

2,4,6,7,8,8a,9,9aβ-octahydro-8aβ-methyl-2-oxonaphtho<2,3-b>furan-3-carboxylic acid methyl ester (73483-60-0) → 3aβ,4,4aα,5,6,7,8,8a,9,9aβ-decahydro-3α,8aβ-dimethyl-5-methylene-3β-(phenylthio)naphtho<2,3-b>furan-2(3H)-one (74064-03-2,74064-04-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) borane-methyl sulphide complex, 2.) 30percent hydrogen peroxide, 2.5M sodium acetate / 1.) ethyl acetate, room temperature, 2 h, 2.) absolute ethanol, room temperature, 6 h

2: 94 percent / Jones reagent / acetone / 0 °C

3: sodium methoxide / methanol / 16 h / Heating

4: 86 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 17 h / Ambient temperature

5: 93 percent / sodium hydride / tetrahydrofuran / 6 h

6: 91 percent / sodium cyanide / hexamethylphosphoric acid triamide / 1 h / 80 °C

7: lithium diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 1 h, 2.) -20 deg C, 30 min, 3.) room temperature, 2 h

With sodium cyanide; jones reagent; dimethylsulfide borane complex; dihydrogen peroxide; sodium methylate; sodium acetate; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; acetone;

DOI:10.1021/ja00527a046

Reference yield:

2,4,6,7,8,8a,9,9aβ-octahydro-8aβ-methyl-2-oxonaphtho<2,3-b>furan-3-carboxylic acid methyl ester (73483-60-0) → 3aβ,4,4aα,5,6,7,8,8a,9,9aβ-decahydro-3β,8aβ-dimethyl-5-methylene-3β-(phenylthio)naphtho<2,3-b>furan-2(3H)-one (74064-03-2,74064-04-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) borane-methyl sulphide complex, 2.) 30percent hydrogen peroxide, 2.5M sodium acetate / 1.) ethyl acetate, room temperature, 2 h, 2.) absolute ethanol, room temperature, 6 h

2: 94 percent / Jones reagent / acetone / 0 °C

3: sodium methoxide / methanol / 16 h / Heating

4: 86 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 17 h / Ambient temperature

5: 93 percent / sodium hydride / tetrahydrofuran / 6 h

6: 91 percent / sodium cyanide / hexamethylphosphoric acid triamide / 1 h / 80 °C

7: lithium diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 1 h, 2.) -20 deg C, 30 min, 3.) room temperature, 2 h

With sodium cyanide; jones reagent; dimethylsulfide borane complex; dihydrogen peroxide; sodium methylate; sodium acetate; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; acetone;

DOI:10.1021/ja00527a046

Reference yield:

2,5,6,7,8,8a,9,9aβ-octahydro-8aβ-methyl-2-oxonaphtho<2,3-b>furan-3-carboxylic acid methyl ester (61082-24-4,70789-75-2,74063-92-6) → 3aβ,4,4aα,5,6,7,8,8a,9,9aβ-decahydro-3α,8aβ-dimethyl-5-methylene-3β-(phenylthio)naphtho<2,3-b>furan-2(3H)-one (74064-03-2,74064-04-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) N-bromosuccinimide / 1.) carbon tetrachloride, 85 deg C, 2.) irradiation, reflux, 20 min

2: 97 percent / zinc dust, glacial acetic acid / tetrahydrofuran / 1 h / Ambient temperature

3: 1.) borane-methyl sulphide complex, 2.) 30percent hydrogen peroxide, 2.5M sodium acetate / 1.) ethyl acetate, room temperature, 2 h, 2.) absolute ethanol, room temperature, 6 h

4: 94 percent / Jones reagent / acetone / 0 °C

5: sodium methoxide / methanol / 16 h / Heating

6: 86 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 17 h / Ambient temperature

7: 93 percent / sodium hydride / tetrahydrofuran / 6 h

8: 91 percent / sodium cyanide / hexamethylphosphoric acid triamide / 1 h / 80 °C

9: lithium diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 1 h, 2.) -20 deg C, 30 min, 3.) room temperature, 2 h

With sodium cyanide; N-Bromosuccinimide; jones reagent; dimethylsulfide borane complex; dihydrogen peroxide; sodium methylate; sodium acetate; sodium hydride; acetic acid; zinc; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; acetone;

DOI:10.1021/ja00527a046

upstream raw materials:

(+/-)-dihydrocallitrisin

diphenyldisulfane

2,3,3aβ,4,6,7,8,8a,9,9aβ-decahydro-8aβ-methyl-2-oxonaphtho<2,3-b>furan-3-carboxylic acid methyl ester

2,3,3aβ,4,4aα,5,6,7,8,8a,9,9aβ-dodecahydro-8aβ-methyl-5-methylenenaphtho<2,3-b>furan-3-carboxylic acid methyl ester

Downstream raw materials:

4aα,5,6,7,8,8a,9,9aβ-octahydro-3-methyl-5-methylenenaphtho<2,3-b>furan-2(4H)-one

dl-7,8-epiisoalantolactone

(+/-)-atractylon