(+/-)-dihydrocallitrisin

Base Information

• Chemical Name: (+/-)-dihydrocallitrisin
• CAS No.: 108667-51-2
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.338
• Mol file: 108667-51-2.mol

Synonyms:

Chemical Property of (+/-)-dihydrocallitrisin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-dihydrocallitrisin

There total 30 articles about (+/-)-dihydrocallitrisin 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: 91.0%

2,3,3aβ,4,4aα,5,6,7,8,8a,9,9aβ-dodecahydro-3,8aβ-dimethyl-5-methylenenaphtho<2,3-b>furan-3-carboxylic acid methyl ester (73483-65-5,73483-66-6) → (+/-)-dihydrocallitrisin (1856-58-2,22415-07-2,58511-33-4,66964-61-2,72523-74-1,77480-20-7,77480-21-8,108667-51-2)

Guidance literature:

With sodium cyanide; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 80 ℃; for 1h;

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) → (+/-)-dihydrocallitrisin (1856-58-2,22415-07-2,58511-33-4,66964-61-2,72523-74-1,77480-20-7,77480-21-8,108667-51-2)

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: 93 percent / sodium hydride / tetrahydrofuran / 6 h

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

With sodium cyanide; jones reagent; dimethylsulfide borane complex; dihydrogen peroxide; sodium methylate; sodium acetate; sodium hydride; 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) → (+/-)-dihydrocallitrisin (1856-58-2,22415-07-2,58511-33-4,66964-61-2,72523-74-1,77480-20-7,77480-21-8,108667-51-2)

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: 93 percent / sodium hydride / tetrahydrofuran / 6 h

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

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

DOI:10.1021/ja00527a046

upstream raw materials:

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

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

methyl iodide

(3aβ,4aβ,8aβ,9aβ)-5-ethylenedioxy-3a,4,4a,5,6,8,8a,9,9a-decahydro-8a-methylnaphtho<2,3-b>furan-2(3H)-one

Downstream raw materials:

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

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