4-[10-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-5,7,9-trimethyl-4-oxo-6-triethylsilanyloxy-dodec-7-enyl]-piperidine-2,6-dione

Base Information

• Chemical Name: 4-[10-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-5,7,9-trimethyl-4-oxo-6-triethylsilanyloxy-dodec-7-enyl]-piperidine-2,6-dione
• CAS No.: 918868-35-6
• Molecular Formula: C₄₉H₈₁NO₇Si₃
• Molecular Weight: 880.441
• Mol file: 918868-35-6.mol

Synonyms:4-[10-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-5,7,9-trimethyl-4-oxo-6-triethylsilanyloxy-dodec-7-enyl]-piperidine-2,6-dione

Chemical Property of 4-[10-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-5,7,9-trimethyl-4-oxo-6-triethylsilanyloxy-dodec-7-enyl]-piperidine-2,6-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[10-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-5,7,9-trimethyl-4-oxo-6-triethylsilanyloxy-dodec-7-enyl]-piperidine-2,6-dione

There total 25 articles about 4-[10-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-5,7,9-trimethyl-4-oxo-6-triethylsilanyloxy-dodec-7-enyl]-piperidine-2,6-dione 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:

(2S)-methyl 3-(tert-butyldiphenylsilyloxy)-2-methoxy-propionate (918868-38-9) → 4-[10-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-5,7,9-trimethyl-4-oxo-6-triethylsilanyloxy-dodec-7-enyl]-piperidine-2,6-dione (918868-35-6)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 90 percent / DIBAL-H / CH₂Cl₂; hexane / 2.5 h / 20 °C

2.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: MgBr₂*OEt₂ / CH₂Cl₂ / 0.67 h / -21 °C

3.2: 87 percent / CH₂Cl₂ / 7 h / -60 °C

4.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

5.1: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 6.5 h / 20 °C

6.1: NaIO₄ / tetrahydrofuran; H₂O / 3 h / 20 °C

7.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.5 h / 0 °C

7.2: 4.77 g / tetrahydrofuran; toluene / 18 h / -78 °C

8.1: 94 percent / DIBAL-H / CH₂Cl₂; hexane / 2 h / 20 °C

9.1: MnO₂ / CH₂Cl₂ / 24 h / 20 °C

10.1: diethyl ether / 16 h / -78 °C

10.2: 80 percent / diethyl ether; H₂O / 24 h / 20 °C

11.1: 90 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

12.1: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

13.1: 80 percent / NaIO₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

14.1: tetrahydrofuran / 0.5 h / -78 °C

15.1: 73 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

16.1: 32 percent / Hoveyda-Grubbs catalyst / CH₂Cl₂ / 72 h / 20 °C

17.1: 96 percent / hydrogen / palladium on carbon / ethyl acetate / 9 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; manganese(IV) oxide; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; hydrogen; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; magnesium bromide; [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; 2.1: Swern oxidation / 7.2: Still-Gennari olefination;

DOI:10.1016/j.tet.2007.02.107

Reference yield:

8-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-9-methoxy-3,5,7-trimethyl-deca-1,5-dien-4-ol (918868-30-1) → 4-[10-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-5,7,9-trimethyl-4-oxo-6-triethylsilanyloxy-dodec-7-enyl]-piperidine-2,6-dione (918868-35-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

2: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

3: 80 percent / NaIO₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

4: tetrahydrofuran / 0.5 h / -78 °C

5: 73 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

6: 32 percent / Hoveyda-Grubbs catalyst / CH₂Cl₂ / 72 h / 20 °C

7: 96 percent / hydrogen / palladium on carbon / ethyl acetate / 9 h / 20 °C

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; hydrogen; Dess-Martin periodane; 4-methylmorpholine N-oxide; [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; tert-butyl alcohol;

DOI:10.1016/j.tet.2007.02.107

Reference yield:

5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-enal (918868-29-8) → 4-[10-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-5,7,9-trimethyl-4-oxo-6-triethylsilanyloxy-dodec-7-enyl]-piperidine-2,6-dione (918868-35-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: diethyl ether / 16 h / -78 °C

1.2: 80 percent / diethyl ether; H₂O / 24 h / 20 °C

2.1: 90 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

3.1: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

4.1: 80 percent / NaIO₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

5.1: tetrahydrofuran / 0.5 h / -78 °C

6.1: 73 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

7.1: 32 percent / Hoveyda-Grubbs catalyst / CH₂Cl₂ / 72 h / 20 °C

8.1: 96 percent / hydrogen / palladium on carbon / ethyl acetate / 9 h / 20 °C

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; hydrogen; Dess-Martin periodane; 4-methylmorpholine N-oxide; [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; tert-butyl alcohol;

DOI:10.1016/j.tet.2007.02.107

upstream raw materials:

(2S)-methyl 3-(tert-butyldiphenylsilyloxy)-2-methoxy-propionate

(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol

5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-enal

5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-en-1-ol

Downstream raw materials:

4-[10-(tert-butyl-dimethyl-silanyloxy)-12-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-11-methoxy-5,7,9-trimethyl-4-oxo-dodec-7-enyl]-piperidine-2,6-dione

hepta-2,6-dienoic acid 5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-1-[5-(2,6-dioxo-piperidin-4-yl)-1-methyl-2-oxo-pentyl]-6-methoxy-2,4-dimethyl-hept-2-enyl ester