7-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6-trimethyl-3-triethylsilanyloxy-non-4-enal

Base Information

• Chemical Name: 7-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6-trimethyl-3-triethylsilanyloxy-non-4-enal
• CAS No.: 918868-32-3
• Molecular Formula: C₄₁H₇₀O₅Si₃
• Molecular Weight: 727.26
• Mol file: 918868-32-3.mol

Synonyms:7-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6-trimethyl-3-triethylsilanyloxy-non-4-enal

Chemical Property of 7-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6-trimethyl-3-triethylsilanyloxy-non-4-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6-trimethyl-3-triethylsilanyloxy-non-4-enal

There total 19 articles about 7-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6-trimethyl-3-triethylsilanyloxy-non-4-enal 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: 80.0%

C42H74O6Si3 → 7-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6-trimethyl-3-triethylsilanyloxy-non-4-enal (918868-32-3)

Guidance literature:

With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2007.02.107

Reference yield:

(2S)-methyl 3-(tert-butyldiphenylsilyloxy)-2-methoxy-propionate (918868-38-9) → 7-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6-trimethyl-3-triethylsilanyloxy-non-4-enal (918868-32-3)

Guidance literature:

Multi-step reaction with 13 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

With 1H-imidazole; 2,6-dimethylpyridine; manganese(IV) oxide; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; magnesium bromide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 2.1: Swern oxidation / 7.2: Still-Gennari olefination;

DOI:10.1016/j.tet.2007.02.107

Reference yield:

(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol (848035-35-8) → 7-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-8-methoxy-2,4,6-trimethyl-3-triethylsilanyloxy-non-4-enal (918868-32-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

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

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

4.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 0.5 h / 0 °C

4.2: 4.77 g / tetrahydrofuran; toluene / 18 h / -78 °C

5.1: 94 percent / DIBAL-H / CH₂Cl₂; hexane / 2 h / 20 °C

6.1: MnO₂ / CH₂Cl₂ / 24 h / 20 °C

7.1: diethyl ether / 16 h / -78 °C

7.2: 80 percent / diethyl ether; H₂O / 24 h / 20 °C

8.1: 90 percent / imidazole / CH₂Cl₂ / 6 h / 20 °C

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

10.1: 80 percent / NaIO₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; manganese(IV) oxide; sodium periodate; osmium(VIII) oxide; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 4.2: Still-Gennari olefination;

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:

9-(tert-butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-10-methoxy-4,6,8-trimethyl-5-triethylsilanyloxy-undeca-1,6-dien-3-one

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

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

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