(1E)(3S)-3-(tert-butyl-dimethylsilyl)oxy-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-diene

Base Information

• Chemical Name: (1E)(3S)-3-(tert-butyl-dimethylsilyl)oxy-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-diene
• CAS No.: 188730-05-4
• Molecular Formula: C₁₇H₂₉NOSSi
• Molecular Weight: 323.575
• Mol file: 188730-05-4.mol

Synonyms:(1E)(3S)-3-(tert-butyl-dimethylsilyl)oxy-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-diene

Chemical Property of (1E)(3S)-3-(tert-butyl-dimethylsilyl)oxy-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1E)(3S)-3-(tert-butyl-dimethylsilyl)oxy-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-diene

There total 1 articles about (1E)(3S)-3-(tert-butyl-dimethylsilyl)oxy-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-diene 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) → (1E)(3S)-3-(tert-butyl-dimethylsilyl)oxy-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-diene (188730-05-4)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; diisobutylaluminium hydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane; benzene;

DOI:10.1021/ja971110h

Reference yield:

(1E)(3S)-3-(tert-butyl-dimethylsilyl)oxy-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-diene (188730-05-4) → epothilone B (152044-54-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: OsO₄

1.2: 80 percent / NaIO₄

2.1: 93 percent / NiCl₂; CrCl₂ / dimethylformamide / 0.67 h / 20 °C

3.1: 87 percent / SOCl₂ / diethyl ether; pentane / 6.5 h / -78 - 0 °C

4.1: 88 percent / LiEt₃BH / tetrahydrofuran / 2 h / -78 - 20 °C

5.1: 80 percent / PCC

6.1: LDA

7.1: 88 percent / CSA / methanol

8.1: PCC

8.2: 90 percent / NaClO₂

9.1: 73 percent / TBAF

10.1: 77 percent / TCBCl; DIEA; DMAP

11.1: 59 percent / HF*pyr

12.1: 65 percent / mCPBA

With chromium dichloride; dmap; osmium(VIII) oxide; thionyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; lithium triethylborohydride; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; nickel dichloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; pentane;

DOI:10.1021/ol010094x

Reference yield:

(1E)(3S)-3-(tert-butyl-dimethylsilyl)oxy-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-diene (188730-05-4) → epothilone D (189453-10-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: OsO₄

1.2: 80 percent / NaIO₄

2.1: 93 percent / NiCl₂; CrCl₂ / dimethylformamide / 0.67 h / 20 °C

3.1: 87 percent / SOCl₂ / diethyl ether; pentane / 6.5 h / -78 - 0 °C

4.1: 88 percent / LiEt₃BH / tetrahydrofuran / 2 h / -78 - 20 °C

5.1: 80 percent / PCC

6.1: LDA

7.1: 88 percent / CSA / methanol

8.1: PCC

8.2: 90 percent / NaClO₂

9.1: 73 percent / TBAF

10.1: 77 percent / TCBCl; DIEA; DMAP

11.1: 59 percent / HF*pyr

With chromium dichloride; dmap; osmium(VIII) oxide; thionyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; lithium triethylborohydride; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; nickel dichloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; pentane;

DOI:10.1021/ol010094x

upstream raw materials:

ethyl 2-methylthiazole-4-carboxylate

Downstream raw materials:

desoxyepothilone A

epothilone B

(4S,7R,8S,9S,13Z,16S,1'E)-4,8-di-tert-butyldimethylsilyloxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-1-oxa-13-cyclohexadecene-2,6-dione

epothilone D