tert-Butyl-[(4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyloxy]-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-[(4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyloxy]-dimethyl-silane
• CAS No.: 623926-63-6
• Molecular Formula: C₅₁H₈₀O₇Si
• Molecular Weight: 833.277
• Mol file: 623926-63-6.mol

Synonyms:tert-Butyl-[(4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyloxy]-dimethyl-silane

Chemical Property of tert-Butyl-[(4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyloxy]-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[(4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyloxy]-dimethyl-silane

There total 19 articles about tert-Butyl-[(4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyloxy]-dimethyl-silane 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:

(Z)-(4R,5R,6S,7S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7-dimethyl-undeca-8,10-dienal (623926-62-5) + [(Z)-(2R,3S,4S)-3-(4-Methoxy-benzyloxy)-2,4-dimethyl-9-(tetrahydro-pyran-2-yloxy)-non-5-enyl]-triphenyl-phosphonium; iodide → tert-Butyl-[(4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyloxy]-dimethyl-silane (623926-63-6)

Guidance literature:

(Z)-(4R,5R,6S,7S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7-dimethyl-undeca-8,10-dienal; With sodium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 0.75h;

[(Z)-(2R,3S,4S)-3-(4-Methoxy-benzyloxy)-2,4-dimethyl-9-(tetrahydro-pyran-2-yloxy)-non-5-enyl]-triphenyl-phosphonium; iodide; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0968-0896(03)00186-X

Reference yield:

(2S,3S,4S)-(1-tert-butyldimethylsilanyloxy)-2,4-dimethylhex-5-en-3-ol (106296-58-6) → tert-Butyl-[(4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyloxy]-dimethyl-silane (623926-63-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 89 percent / NaH / tetrahydrofuran; dimethylformamide / 48 h / 20 °C

2.1: ozone; pyridine / CH₂Cl₂; methanol / -78 °C

2.2: dimethyl sulfide / CH₂Cl₂; methanol / -78 - 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.83 h / 20 °C

3.2: 0.55 g / tetrahydrofuran / -78 - 20 °C

4.1: 89 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

5.1: 92 percent / I₂; PPh₃; imidazole / benzene; diethyl ether

6.1: 75 percent / benzene / 80 °C

7.1: NaHMDS / tetrahydrofuran / 0.75 h / 20 °C

7.2: tetrahydrofuran / -78 - 20 °C

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; sodium hydride; ozone; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 3.2: Wittig reaction / 7.2: Wittig reaction;

DOI:10.1016/S0968-0896(03)00186-X

Reference yield:

(2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene (184291-95-0) → tert-Butyl-[(4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyloxy]-dimethyl-silane (623926-63-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: ozone; pyridine / CH₂Cl₂; methanol / -78 °C

1.2: dimethyl sulfide / CH₂Cl₂; methanol / -78 - 20 °C

2.1: NaHMDS / tetrahydrofuran / 0.83 h / 20 °C

2.2: 0.55 g / tetrahydrofuran / -78 - 20 °C

3.1: 89 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

4.1: 92 percent / I₂; PPh₃; imidazole / benzene; diethyl ether

5.1: 75 percent / benzene / 80 °C

6.1: NaHMDS / tetrahydrofuran / 0.75 h / 20 °C

6.2: tetrahydrofuran / -78 - 20 °C

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; ozone; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene; 2.2: Wittig reaction / 6.2: Wittig reaction;

DOI:10.1016/S0968-0896(03)00186-X

upstream raw materials:

(Z)-(4R,5R,6S,7S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7-dimethyl-undeca-8,10-dienal

{4-[(tetrahydropyran-2-yl)oxy]butyl}(triphenyl)phosphonium iodide

(2S,3S,4S)-(1-tert-butyldimethylsilanyloxy)-2,4-dimethylhex-5-en-3-ol

(2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene

Downstream raw materials:

Acetic acid (4Z,9Z)-(1R,6S,7S,8S)-13-hydroxy-7-(4-methoxy-benzyloxy)-1-[(Z)-(1S,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-trideca-4,9-dienyl ester

Carbamic acid (4Z,9Z)-(1R,6S,7S,8S)-13-hydroxy-7-(4-methoxy-benzyloxy)-1-[(Z)-(1S,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-trideca-4,9-dienyl ester

acetic acid (Z,Z,Z)-(6S,7S,8S,13R,14S,15S,16S)-13-carbamoyloxy-7,15-bis(4-methoxybenzyloxy)-6,8,14,16-tetramethyleicosa-4,9,17,19-tetraenyl ester

2,2-dimethylpropionic acid (Z,Z,Z)-(6S,7S,8S,13R,14S,15S,16S)-13-acetoxy-7,15-bis(4-methoxybenzyloxy)-6,8,14,16-tetramethyleicosa-4,9,17,19-tetraenyl ester