(2E,4S,6S,7S,8R,9E,11E,13E)-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-1-al

Base Information

• Chemical Name: (2E,4S,6S,7S,8R,9E,11E,13E)-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-1-al
• CAS No.: 237735-31-8
• Molecular Formula: C₃₉H₅₆N₂O₈Si
• Molecular Weight: 708.968
• Mol file: 237735-31-8.mol

Synonyms:(2E,4S,6S,7S,8R,9E,11E,13E)-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-1-al

Chemical Property of (2E,4S,6S,7S,8R,9E,11E,13E)-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-1-al

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4S,6S,7S,8R,9E,11E,13E)-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-1-al

There total 24 articles about (2E,4S,6S,7S,8R,9E,11E,13E)-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-1-al 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: 82.0%

(2E,4S,6S,7S,8R,9E,11E,13E)-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-1-ol (237735-43-2) → (2E,4S,6S,7S,8R,9E,11E,13E)-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-1-al (237735-31-8)

Guidance literature:

With Dess-Martin periodane;

DOI:10.1016/S0040-4039(99)00731-5

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (2E,4S,6S,7S,8R,9E,11E,13E)-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-1-al (237735-31-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 99 percent / 2,6-lutidine

2: 89 percent / DIBAL

3: 1) Et₃N, 2) imidazol, 3) DIBAL

4: 90 percent / Dess-Martin reagent

5: 100 percent

6: 96 percent / Dess-Martin reagent

7: 85 percent / Ba(OH)2*H₂O

8: 86 percent / H₂SiF₆ / propan-2-ol / -40 °C

9: 83 percent / SmI₂

10: 77 percent / Ag₂O / ultrasonication

11: 94 percent / H₂SiF₆ / acetonitrile; 2-methyl-propan-2-ol

12: 82 percent / Dess-Martin reagent

With 1H-imidazole; 2,6-dimethylpyridine; barium dihydroxide; fluorosilicic acid; samarium diiodide; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; silver(l) oxide; In isopropyl alcohol; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(99)00731-5

Reference yield:

(E)-4-(t-butyl-dimethyl-silanyloxy)-2-methyl-but-2-enal (144950-82-3) → (2E,4S,6S,7S,8R,9E,11E,13E)-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-1-al (237735-31-8)

Guidance literature:

Multi-step reaction with 16 steps

1.1: diisopropylamine; n-BuLi / tetrahydrofuran / 1 h / -78 °C

1.2: 78 percent / tetrahydrofuran / 0.08 h

2.1: (-)-diisopropyl tartrate; Ti(O-iPr)4; tert-butylhydroperoxide / molecular sieves 3 Angstroem / CH₂Cl₂ / 20 h / -20 °C

2.2: 40 percent / FeSO₄; citric acid / H₂O; CH₂Cl₂

3.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

4.1: 89 percent / DIBAL-H / CH₂Cl₂; toluene / 0.25 h / -95 °C

5.1: triethylamine; dicyclohexylboron triflate / CH₂Cl₂; hexane / 2 h / -78 °C

5.2: CH₂Cl₂; hexane / 3 h / -78 - 0 °C

5.3: 81 percent / NaOAc; water; H₂O₂ / CH₂Cl₂; hexane; methanol / 12 h

6.1: 86 percent / imidazole / CH₂Cl₂ / 0.08 h / 0 °C

7.1: 100 percent / DIBAL-H / CH₂Cl₂; toluene / 0.08 h / 0 °C

8.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

9.1: t-BuLi / tetrahydrofuran; pentane / 0.75 h / -78 °C

9.2: 100 percent / tetrahydrofuran; pentane / 0.17 h

10.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 °C

11.1: Ba(OH)2 / tetrahydrofuran / 0.5 h / 20 °C

11.2: 85 percent / tetrahydrofuran; H₂O / 48 h

12.1: 86 percent / H₂SiF₆ / propan-2-ol; H₂O / 0.02 h / -40 °C

13.1: 83 percent / SmI₂ / tetrahydrofuran / 3.5 h / -10 °C

14.1: 77 percent / Ag₂O; molecular sieves 3 Angstroem / benzene / 12 h / sonication

15.1: 94 percent / H₂SiF₆ / acetonitrile; 2-methyl-propan-2-ol; H₂O / 21 h / 0 °C

16.1: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 0 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; barium dihydroxide; n-butyllithium; fluorosilicic acid; samarium diiodide; (-)-diisopropyl tartrate; 3 A molecular sieve; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; diisopropylamine; silver(l) oxide; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; 3 A molecular sieve; In tetrahydrofuran; hexane; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile; tert-butyl alcohol; pentane; benzene;

DOI:10.1021/jo034011x

upstream raw materials:

(2E,4S,6S,7S,8R,9E,11E,13E)-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-1-ol

2-methyl-1,3-oxazole-4-carbaldehyde

(1'E,3'E)-2-methyl-4-(2'-methyl-5'-oxo-1',3'-pentadienyl)-oxazole

(1'E,3'E)-4-(5'-Hydroxy-2'-methyl-1',3'-pentadienyl)-2-methyloxazole

Downstream raw materials:

4-nitro-benzoic acid 1-{7-[6-(tert-butyl-dimethyl-silanyloxy)-4-(2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-yl]-3-methyl-2-triisopropylsilanyloxy-octa-3,5-dienyl}-3-methoxy-2,4,8-trimethyl-9-(2-methyl-oxazol-4-yl)-nona-4,6,8-trienyl ester

4-nitro-benzoic acid 1-{7-[4-(3-ethoxycarbonyl-allyl)-6-methoxy-tetrahydro-pyran-2-yl]-3-methyl-2-triisopropylsilanyloxy-octa-3,5-dienyl}-3-methoxy-2,4,8-trimethyl-9-(2-methyl-oxazol-4-yl)-nona-4,6,8-trienyl ester