(8E,12E)-(2S,6S,7S,10S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-2-ethyl-2,7-bis-(4-methoxy-benzyloxy)-6,8,10,12-tetramethyl-3-oxo-tetradeca-8,12-dienoic acid methyl ester

Base Information

• Chemical Name: (8E,12E)-(2S,6S,7S,10S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-2-ethyl-2,7-bis-(4-methoxy-benzyloxy)-6,8,10,12-tetramethyl-3-oxo-tetradeca-8,12-dienoic acid methyl ester
• CAS No.: 180285-54-5
• Molecular Formula: C₅₃H₇₀O₈Si
• Molecular Weight: 863.219

Synonyms:(8E,12E)-(2S,6S,7S,10S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-2-ethyl-2,7-bis-(4-methoxy-benzyloxy)-6,8,10,12-tetramethyl-3-oxo-tetradeca-8,12-dienoic acid methyl ester

Chemical Property of (8E,12E)-(2S,6S,7S,10S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-2-ethyl-2,7-bis-(4-methoxy-benzyloxy)-6,8,10,12-tetramethyl-3-oxo-tetradeca-8,12-dienoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8E,12E)-(2S,6S,7S,10S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-2-ethyl-2,7-bis-(4-methoxy-benzyloxy)-6,8,10,12-tetramethyl-3-oxo-tetradeca-8,12-dienoic acid methyl ester

There total 8 articles about (8E,12E)-(2S,6S,7S,10S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-2-ethyl-2,7-bis-(4-methoxy-benzyloxy)-6,8,10,12-tetramethyl-3-oxo-tetradeca-8,12-dienoic acid methyl ester 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: 96.0%

(8E,12E)-(2S,6S,7S,10S,11R)-4-Benzenesulfonyl-11-(tert-butyl-diphenyl-silanyloxy)-2-ethyl-2,7-bis-(4-methoxy-benzyloxy)-6,8,10,12-tetramethyl-3-oxo-tetradeca-8,12-dienoic acid methyl ester → (8E,12E)-(2S,6S,7S,10S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-2-ethyl-2,7-bis-(4-methoxy-benzyloxy)-6,8,10,12-tetramethyl-3-oxo-tetradeca-8,12-dienoic acid methyl ester (180285-54-5)

Guidance literature:

With aluminium amalgam; In tetrahydrofuran; water;

DOI:10.1016/0040-4039(96)00804-0

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (8E,12E)-(2S,6S,7S,10S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-2-ethyl-2,7-bis-(4-methoxy-benzyloxy)-6,8,10,12-tetramethyl-3-oxo-tetradeca-8,12-dienoic acid methyl ester (180285-54-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / PPTS / dimethylformamide / 2 h / 55 °C / 25 Torr

2: i-Bu₂AlH / CH₂Cl₂ / 2 h / -78 °C

3: pyridinium dichromate / dimethylformamide / 96 h / Ambient temperature

4: diethyl ether; CHCl₃

5: 74 percent / n-Bu₄NF / tetrahydrofuran / 48 h / Ambient temperature

6: 82 percent / 1.) Me₂SO, (COCl)2; 2.) Et₃N / CH₂Cl₂ / -78 °C

7: 82 percent / n-BuLi / tetrahydrofuran / -78 °C

8: 93 percent / Me₂SO, (CF₃CO)2O / CH₂Cl₂ / -78 °C

9: 96 percent / aluminum amalgam / H₂O; tetrahydrofuran

With dipyridinium dichromate; n-butyllithium; oxalyl dichloride; aluminium amalgam; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(96)00804-0

Reference yield:

(S)-2-Hydroxymethyl-2-(4-methoxy-benzyloxy)-butyric acid methyl ester (180285-51-2) → (8E,12E)-(2S,6S,7S,10S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-2-ethyl-2,7-bis-(4-methoxy-benzyloxy)-6,8,10,12-tetramethyl-3-oxo-tetradeca-8,12-dienoic acid methyl ester (180285-54-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / 1.) Me₂SO, (COCl)2; 2.) Et₃N / CH₂Cl₂ / -78 °C

2: 82 percent / n-BuLi / tetrahydrofuran / -78 °C

3: 93 percent / Me₂SO, (CF₃CO)2O / CH₂Cl₂ / -78 °C

4: 96 percent / aluminum amalgam / H₂O; tetrahydrofuran

With n-butyllithium; oxalyl dichloride; aluminium amalgam; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/0040-4039(96)00804-0

upstream raw materials:

p-Anisaldehyde dimethyl acetal

(S)-2-Hydroxymethyl-2-(4-methoxy-benzyloxy)-butyric acid methyl ester

(S)-2-Formyl-2-(4-methoxy-benzyloxy)-butyric acid methyl ester

(R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-butan-1-ol

Downstream raw materials:

(S)-2-{(5S,6S)-6-[(1E,5E)-(3S,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-1,3,5-trimethyl-hepta-1,5-dienyl]-5-methyl-5,6-dihydro-4H-pyran-2-yl}-2-(4-methoxy-benzyloxy)-butyric acid methyl ester

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