(2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal

Base Information

• Chemical Name: (2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal
• CAS No.: 193146-27-9
• Molecular Formula: C₂₄H₄₁NO₂SSi
• Molecular Weight: 435.747

Synonyms:(2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal

Chemical Property of (2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal

There total 1 articles about (2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal 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) → (2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal (193146-27-9)

Guidance literature:

Multi-step reaction with 15 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: 95 percent / benzene / 3 h / Heating

8: 98 percent / DIBAL / tetrahydrofuran; CH₂Cl₂ / 3 h / -78 °C

9: 83 percent / Ph₃P, CCl₄ / 24 h / 100 °C

10: 99 percent / LiEt₃BH / tetrahydrofuran / 1 h / 0 °C

11: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C

12: 92 percent / I₂, imidazole, Ph₃P / diethyl ether; acetonitrile / 0.5 h / 0 °C

13: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h

14: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C

15: 82 percent / DIBAL / toluene / 1 h / -78 °C

With 1H-imidazole; lead(IV) acetate; tetrachloromethane; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; iodine; diisobutylaluminium hydride; lithium triethylborohydride; 4-methylmorpholine N-oxide; Monoperoxyphthalic acid, magnesium salt; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; pentane; benzene;

DOI:10.1021/ja971110h

Reference yield: 83.0%

C21H34O4Si (1174394-77-4) + (2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal (193146-27-9) → C45H75NO6SSi2

Guidance literature:

C₂₁H₃₄O₄Si; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.0333333h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; Inert atmosphere;

(2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.3390/ijms18030648

Reference yield:

(2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal (193146-27-9) → epothilone B (152044-54-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: LDA

2.1: 88 percent / CSA / methanol

3.1: PCC

3.2: 90 percent / NaClO₂

4.1: 73 percent / TBAF

5.1: 77 percent / TCBCl; DIEA; DMAP

6.1: 59 percent / HF*pyr

7.1: 65 percent / mCPBA

With dmap; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diisopropyl amide; In methanol;

DOI:10.1021/ol010094x

upstream raw materials:

ethyl 2-methylthiazole-4-carboxylate

Downstream raw materials:

(7S,10R,11S,12S,19S,Z)-7-(tert-butyldimethylsilyloxy)-11-hydroxy-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one

(12Z,16E)-(3S,6R,7S,8S,15S)-3,7,15-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid

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

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