4-[(1E,5Z)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-undeca-1,5-dienyl]-2-methyl-thiazole

Base Information

• Chemical Name: 4-[(1E,5Z)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-undeca-1,5-dienyl]-2-methyl-thiazole
• CAS No.: 188730-11-2
• Molecular Formula: C₂₉H₅₅NO₂SSi₂
• Molecular Weight: 537.998
• Mol file: 188730-11-2.mol

Synonyms:4-[(1E,5Z)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-undeca-1,5-dienyl]-2-methyl-thiazole

Chemical Property of 4-[(1E,5Z)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-undeca-1,5-dienyl]-2-methyl-thiazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(1E,5Z)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-undeca-1,5-dienyl]-2-methyl-thiazole

There total 1 articles about 4-[(1E,5Z)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-undeca-1,5-dienyl]-2-methyl-thiazole 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:

ethyl 2-methylthiazole-4-carboxylate (6436-59-5) → 4-[(1E,5Z)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-undeca-1,5-dienyl]-2-methyl-thiazole (188730-11-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

2: 98 percent / benzene / 2 h / Heating

3: 74 percent / diethyl ether; pentane / 1 h / -100 °C

4: 99 percent / imidazole / dimethylformamide / 1) 0 deg C, 45 min, 2) 25 deg C, 2.5 h

5: 95 percent / 4-methylmorpholine N-oxide, OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 1) 0 deg C, 2.5 h, 2) 25 deg C, 12 h

6: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C

7: 1) NaHMDS / 1) THF, 0 deg C, 15 min, 2) THF, 0 deg C, 15 min

With 1H-imidazole; lead(IV) acetate; osmium(VIII) oxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; pentane; benzene;

DOI:10.1021/ja971110h

Reference yield:

4-[(1E,5Z)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-undeca-1,5-dienyl]-2-methyl-thiazole (188730-11-2) → desoxyepothilone A (186692-73-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 86 percent / CSA / CH₂Cl₂; methanol / 1.) 0 deg C, 1 h, 2.) 25 deg C, 0.5 h

2: 82 percent / SO₃*pyridine, DMSO, Et₃N / CH₂Cl₂ / 0.5 h / 25 °C

3: LDA / tetrahydrofuran / 1.) -78 to -40 deg C, 0.5 h, 2.) -78 deg C

4: 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

5: K₂CO₃ / methanol / 0.25 h / 25 °C

6: 79 percent / TBAF / tetrahydrofuran / 8 h / 25 °C

7: 1.) 2,4,6-trichlorobenzoylchloride, Et₃N, 2.) 4-DMAP / 1.) THF, 25 deg C, 15 min, 2.) toluene, 25 deg C, 0.5 h

8: 92 percent / CF₃COOH / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; dmap; pyridine-SO₃ complex; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/anie.199705251

upstream raw materials:

ethyl 2-methylthiazole-4-carboxylate

Downstream raw materials:

desoxyepothilone A