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

Base Information

• Chemical Name: 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
• CAS No.: 544429-56-3
• Molecular Formula: C₅₄H₈₀N₂O₁₁Si
• Molecular Weight: 961.322
• Mol file: 544429-56-3.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 41 articles about 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 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: 81.0%

(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-al (237735-31-8) + (E)-4-{(2R,4R)-2-[(S)-2-(Benzothiazole-2-sulfonyl)-1-methyl-ethyl]-6-methoxy-tetrahydro-pyran-4-yl}-but-2-enoic acid ethyl ester (544429-55-2) → 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 (544429-56-3)

Guidance literature:

With lithium hexamethyldisilazane;

DOI:10.1021/jo034011x

Reference yield:

(E)-4-(t-butyl-dimethyl-silanyloxy)-2-methyl-but-2-enal (144950-82-3) → 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 (544429-56-3)

Guidance literature:

Multi-step reaction with 17 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

17.1: 81 percent / LiHMDS

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; lithium hexamethyldisilazane; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; 3 A molecular sieve; In tetrahydrofuran; hexane; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile; tert-butyl alcohol; pentane; benzene; 17.1: Julia coupling;

DOI:10.1021/jo034011x

Reference yield:

methyl (4E)-6-[(t-butyldimethylsilyl)oxy]-4-methyl-3-hydroxy-4-hexenoate (237735-58-9) → 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 (544429-56-3)

Guidance literature:

Multi-step reaction with 16 steps

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

1.2: 40 percent / FeSO₄; citric acid / H₂O; CH₂Cl₂

2.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

3.1: 89 percent / DIBAL-H / CH₂Cl₂; toluene / 0.25 h / -95 °C

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

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

4.3: 81 percent / NaOAc; water; H₂O₂ / CH₂Cl₂; hexane; methanol / 12 h

5.1: 86 percent / imidazole / CH₂Cl₂ / 0.08 h / 0 °C

6.1: 100 percent / DIBAL-H / CH₂Cl₂; toluene / 0.08 h / 0 °C

7.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

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

8.2: 100 percent / tetrahydrofuran; pentane / 0.17 h

9.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 °C

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

10.2: 85 percent / tetrahydrofuran; H₂O / 48 h

11.1: 86 percent / H₂SiF₆ / propan-2-ol; H₂O / 0.02 h / -40 °C

12.1: 83 percent / SmI₂ / tetrahydrofuran / 3.5 h / -10 °C

13.1: 77 percent / Ag₂O; molecular sieves 3 Angstroem / benzene / 12 h / sonication

14.1: 94 percent / H₂SiF₆ / acetonitrile; 2-methyl-propan-2-ol; H₂O / 21 h / 0 °C

15.1: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 0 - 20 °C

16.1: 81 percent / LiHMDS

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; barium dihydroxide; fluorosilicic acid; samarium diiodide; (-)-diisopropyl tartrate; 3 A molecular sieve; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; silver(l) oxide; lithium hexamethyldisilazane; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; 3 A molecular sieve; In tetrahydrofuran; hexane; dichloromethane; water; isopropyl alcohol; toluene; acetonitrile; tert-butyl alcohol; pentane; benzene; 16.1: Julia coupling;

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-al

(E)-4-{(2R,4R)-2-[(S)-2-(Benzothiazole-2-sulfonyl)-1-methyl-ethyl]-6-methoxy-tetrahydro-pyran-4-yl}-but-2-enoic acid ethyl ester

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

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

Refernces