4-Pentenal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methyl-5-(2-methyl-4-thiazolyl)- , (3S,4E)-

Base Information

• Chemical Name: 4-Pentenal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methyl-5-(2-methyl-4-thiazolyl)- , (3S,4E)-
• CAS No.: 188730-08-7
• Molecular Formula: C16H27NO2SSi
• Molecular Weight: 325.547
• Mol file: 188730-08-7.mol

Synonyms:(3S,4E)-3-[(tert-Butyldimethylsilyl)oxy]-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)-4-pentenal;(S,4E)-3-(tert-Butyldimethylsilyloxy)-4-methyl-5-(2-methyl-thiazol-4-yl)-pent-4-enal;(3S,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-4-methyl-5-(2-methylthiazol-4-yl)pent-4-enal;(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-5-(2-methyl-thiazol-4-yl)-pent-4-enal;(3S,4E)-3-(tert-Butyldimethylsilyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)-4-pentenal;(S,4E)-3-(tert-butyldimethylsilyloxy)-4-methyl-5-(2-methylthiazol-4-yl)-pent-4-en-1-al;(3S,4E)-3-(tert-butyldimethylsilanyloxy)-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)-pent-4-enal;

Chemical Property of 4-Pentenal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methyl-5-(2-methyl-4-thiazolyl)- , (3S,4E)-

Chemical Property:

• PSA: 67.43000
• LogP: 4.83420

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Pentenal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methyl-5-(2-methyl-4-thiazolyl)- , (3S,4E)-

There total 1 articles about 4-Pentenal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methyl-5-(2-methyl-4-thiazolyl)- , (3S,4E)- 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) → (3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al (188730-08-7)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; lead(IV) acetate; osmium(VIII) oxide; 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: 93.0%

(3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al (188730-08-7) + (S)-4-Benzyl-3-((S)-6-iodo-2-methyl-hept-6-enoyl)-oxazolidin-2-one (355009-02-8) → (S)-4-Benzyl-3-[(E)-(2S,9S)-9-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-2,10-dimethyl-6-methylene-11-(2-methyl-thiazol-4-yl)-undec-10-enoyl]-oxazolidin-2-one (355009-06-2)

Guidance literature:

With chromium dichloride; nickel dichloride; In N,N-dimethyl-formamide; at 20 ℃; for 0.666667h;

DOI:10.1021/ol010094x

Reference yield:

(3S,4E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-5-(2-methyl-1,3-thiazol-4-yl)pent-4-en-1-al (188730-08-7) → epothilone B (152044-54-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 100 percent / HF-pyridine / tetrahydrofuran / 12 h / 20 °C

2.1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 6 h / 20 °C

3.1: 9-BBN / tetrahydrofuran / 1.5 h / 28 °C / microwave irradiation

3.2: 37 percent / K₃PO₄*3H₂O; H₂O / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide / 1 h / 60 °C

4.1: 93 percent / aq. NaOH / methanol / 36 h / 50 °C

5.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C

5.2: 90 percent / DMAP / toluene; tetrahydrofuran / 1 h

6.1: 92 percent / HF*pyridine / tetrahydrofuran

7.1: 97 percent / 3,3-dimethyldioxirane / CH₂Cl₂ / -35 °C

With dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 2,4,6-trichlorobenzoyl chloride; 3,3-dimethyldioxirane; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja002024b

upstream raw materials:

ethyl 2-methylthiazole-4-carboxylate

Downstream raw materials:

ethyl (2Z,5S,6E)-5-{[tert-butyl(dimethyl)silyl]oxy}-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienoate

(S)-4-Benzyl-3-[(E)-(2S,9S)-9-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-2,10-dimethyl-6-methylene-11-(2-methyl-thiazol-4-yl)-undec-10-enoyl]-oxazolidin-2-one

desoxyepothilone A

epothilone B