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

Base Information

• Chemical Name: 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
• CAS No.: 918868-37-8
• Molecular Formula: C₅₀H₇₅NO₈Si₂
• Molecular Weight: 874.318

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 28 articles about 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 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: 74.0%

C14H11Cl3O3 (872513-16-1) + 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 (918868-40-3) → 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 (918868-37-8)

Guidance literature:

With pyridine; In toluene; at 20 ℃; for 48h;

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) → 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 (918868-37-8)

Guidance literature:

Multi-step reaction with 16 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

11.1: tetrahydrofuran / 0.5 h / -78 °C

12.1: 73 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

13.1: 32 percent / Hoveyda-Grubbs catalyst / CH₂Cl₂ / 72 h / 20 °C

14.1: 96 percent / hydrogen / palladium on carbon / ethyl acetate / 9 h / 20 °C

15.1: 80 percent / aq. acetic acid / tetrahydrofuran / 6 h / 20 °C

16.1: 74 percent / pyridine / toluene / 48 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; manganese(IV) oxide; sodium periodate; osmium(VIII) oxide; 18-crown-6 ether; hydrogen; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; 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; hexane; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; 4.2: Still-Gennari olefination;

DOI:10.1016/j.tet.2007.02.107

Reference yield:

(2S)-methyl 3-(tert-butyldiphenylsilyloxy)-2-methoxy-propionate (918868-38-9) → 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 (918868-37-8)

Guidance literature:

Multi-step reaction with 19 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

18.1: 80 percent / aq. acetic acid / tetrahydrofuran / 6 h / 20 °C

19.1: 74 percent / pyridine / toluene / 48 h / 20 °C

With pyridine; 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; acetic acid; 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

upstream raw materials:

C₁₄H₁₁Cl₃O₃

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

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

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

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