dl-7,8-epiisoalantolactone

Base Information

• Chemical Name: dl-7,8-epiisoalantolactone
• CAS No.: 88903-85-9
• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.323
• Mol file: 88903-85-9.mol

Synonyms:

Chemical Property of dl-7,8-epiisoalantolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dl-7,8-epiisoalantolactone

There total 13 articles about dl-7,8-epiisoalantolactone 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:

(3aR,4aS,8aR,9aS)-3,8a-Dimethyl-5-methylene-3-phenylsulfanyl-decahydro-naphtho[2,3-b]furan-2-one (74064-03-2,74064-04-3) → 4aα,5,6,7,8,8a,9,9aβ-octahydro-3-methyl-5-methylenenaphtho<2,3-b>furan-2(4H)-one (3241-66-5,16641-51-3,73069-14-4,74111-89-0,94163-11-8) + dl-7,8-epiisoalantolactone (470-17-7,4677-48-9,22152-49-4,74111-88-9,88903-85-9,102260-71-9,107439-69-0) + (3R,3aR,4aS,8aR,9aS)-3-Benzenesulfinyl-3,8a-dimethyl-5-methylene-decahydro-naphtho[2,3-b]furan-2-one + (3R,3aS,4aR,8aS,9aR)-3-Benzenesulfinyl-3,8a-dimethyl-5-methylene-decahydro-naphtho[2,3-b]furan-2-one

Guidance literature:

With sodium periodate; calcium carbonate; Yield given. Multistep reaction; 1.) THF, water, room temperature, 48 h, 2.) benzene, reflux, 18 h;

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) → dl-7,8-epiisoalantolactone (470-17-7,4677-48-9,22152-49-4,74111-88-9,88903-85-9,102260-71-9,107439-69-0)

Guidance literature:

Multi-step reaction with 6 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: aq. methanolic sodium hydroxide

6: 1.) diethylamine, 2.) sodium acetate, acetic acid / 1.) water

With sodium hydroxide; jones reagent; dimethylsulfide borane complex; dihydrogen peroxide; sodium methylate; sodium acetate; acetic acid; diethylamine; 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) → dl-7,8-epiisoalantolactone (470-17-7,4677-48-9,22152-49-4,74111-88-9,88903-85-9,102260-71-9,107439-69-0)

Guidance literature:

Multi-step reaction with 8 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: aq. methanolic sodium hydroxide

8: 1.) diethylamine, 2.) sodium acetate, acetic acid / 1.) water

With sodium hydroxide; N-Bromosuccinimide; jones reagent; dimethylsulfide borane complex; dihydrogen peroxide; sodium methylate; sodium acetate; acetic acid; diethylamine; zinc; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; acetone;

DOI:10.1021/ja00527a046

upstream raw materials:

formaldehyd

(3aR,4aS,8aR,9aS)-3,8a-Dimethyl-5-methylene-3-phenylsulfanyl-decahydro-naphtho[2,3-b]furan-2-one

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