(E)-(4R,12S,13R)-13-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradeca-1,8-dien-7-ol

Base Information

• Chemical Name: (E)-(4R,12S,13R)-13-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradeca-1,8-dien-7-ol
• CAS No.: 340185-18-4
• Molecular Formula: C₃₁H₅₄O₄Si
• Molecular Weight: 518.853

Synonyms:(E)-(4R,12S,13R)-13-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradeca-1,8-dien-7-ol

Chemical Property of (E)-(4R,12S,13R)-13-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradeca-1,8-dien-7-ol

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,12S,13R)-13-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradeca-1,8-dien-7-ol

There total 12 articles about (E)-(4R,12S,13R)-13-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradeca-1,8-dien-7-ol 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: 68.0%

1-[(S)-1-(2-Iodo-ethyl)-1-methyl-but-3-enyloxymethyl]-4-methoxy-benzene (340185-13-9) + (E)-(6S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-oct-2-enal (340185-11-7) → (E)-(4R,12S,13R)-13-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradeca-1,8-dien-7-ol (340185-18-4)

Guidance literature:

1-[(S)-1-(2-Iodo-ethyl)-1-methyl-but-3-enyloxymethyl]-4-methoxy-benzene; With sec.-butyllithium; In diethyl ether; at -78 ℃; for 0.166667h;

(E)-(6S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-oct-2-enal; In diethyl ether; for 0.166667h;

DOI:10.1002/1521-3773(20010302)40:5<901::AID-ANIE901>3.0.CO;2-F

Reference yield:

<2R,3S>-3-methyl-4-penten-2-ol (74080-51-6) → (E)-(4R,12S,13R)-13-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradeca-1,8-dien-7-ol (340185-18-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 100 percent / imidazole; DMAP / dimethylformamide / 20 °C

2.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

2.2: 85 percent / aq. K₃PO₄ / [PdCl₂(bis(diphenylphosphanyl)ferrocene)] / dimethylformamide / 5 h / 25 °C

3.1: 89 percent / aq. HF; pyridine / 20 °C

4.1: 96 percent / MnO₂ / CH₂Cl₂ / 20 °C

5.1: sec-BuLi / diethyl ether / 0.17 h / -78 °C

5.2: 68 percent / diethyl ether / 0.17 h

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; 9-borabicyclo[3.3.1]nonane dimer; hydrogen fluoride; sec.-butyllithium; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20010302)40:5<901::AID-ANIE901>3.0.CO;2-F

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (E)-(4R,12S,13R)-13-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-4,8,12-trimethyl-tetradeca-1,8-dien-7-ol (340185-18-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 100 percent / imidazole; DMAP / dimethylformamide / 20 °C

2.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

2.2: 85 percent / aq. K₃PO₄ / [PdCl₂(bis(diphenylphosphanyl)ferrocene)] / dimethylformamide / 5 h / 25 °C

3.1: 89 percent / aq. HF; pyridine / 20 °C

4.1: 96 percent / MnO₂ / CH₂Cl₂ / 20 °C

5.1: sec-BuLi / diethyl ether / 0.17 h / -78 °C

5.2: 68 percent / diethyl ether / 0.17 h

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; 9-borabicyclo[3.3.1]nonane dimer; hydrogen fluoride; sec.-butyllithium; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20010302)40:5<901::AID-ANIE901>3.0.CO;2-F

upstream raw materials:

1-[(S)-1-(2-Iodo-ethyl)-1-methyl-but-3-enyloxymethyl]-4-methoxy-benzene

(E)-(6S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-oct-2-enal

<2R,3S>-3-methyl-4-penten-2-ol

tert-butyldimethylsilyl chloride

Downstream raw materials:

(3E,9E)-(5R,8R,13S,14R)-8-(tert-Butyl-diphenyl-silanyloxy)-5-(4-methoxy-benzyloxy)-5,9,13,14-tetramethyl-oxacyclotetradeca-3,9-dien-2-one

(3E,9E)-(5R,8S,13S,14R)-8-(tert-Butyl-diphenyl-silanyloxy)-5-(4-methoxy-benzyloxy)-5,9,13,14-tetramethyl-oxacyclotetradeca-3,9-dien-2-one

(E)-(5R,8R,13S,14R)-8-(tert-Butyl-diphenyl-silanyloxy)-5-(4-methoxy-benzyloxy)-5,9,13,14-tetramethyl-oxacyclotetradec-9-en-2-one

(E)-(5R,8S,13S,14R)-8-(tert-Butyl-diphenyl-silanyloxy)-5-(4-methoxy-benzyloxy)-5,9,13,14-tetramethyl-oxacyclotetradec-9-en-2-one

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