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

Base Information

• Chemical Name: 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
• CAS No.: 237735-34-1
• Molecular Formula: C₆₁H₁₀₂N₂O₁₀Si₃
• Molecular Weight: 1107.74
• Mol file: 237735-34-1.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 46 articles about 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 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: 79.0%

2-{(S)-2-[(2R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-yl]-propane-1-sulfonyl}-benzothiazole (237735-27-2) + (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) → 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 (237735-34-1)

Guidance literature:

With lithium hexamethyldisilazane; at -78 - 20 ℃;

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

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → 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 (237735-34-1)

Guidance literature:

Multi-step reaction with 13 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

13: 79 percent / LiHMDS / -78 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; barium dihydroxide; fluorosilicic acid; samarium diiodide; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; silver(l) oxide; lithium hexamethyldisilazane; 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) → 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 (237735-34-1)

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: 79 percent / LiHMDS / tetrahydrofuran / -78 - 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; 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 olefination;

DOI:10.1021/jo034011x

upstream raw materials:

2-{(S)-2-[(2R,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-4-(2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-yl]-propane-1-sulfonyl}-benzothiazole

(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

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

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

Refernces

• 1、 Lafontaine, Jennifer A.,Provencal, David P.,Gardelli, Cristina,Leahy, James W.. "The enantioselective total synthesis of the antitumor macrolide natural product rhizoxin D". . p. 4145 - 4148. Retrieved 2007/10/03.