(6Z,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2,6,10-trimethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienenitrile

Base Information

• Chemical Name: (6Z,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2,6,10-trimethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienenitrile
• CAS No.: 193146-46-2
• Molecular Formula: C₂₄H₄₀N₂OSSi
• Molecular Weight: 432.746

Synonyms:(6Z,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2,6,10-trimethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienenitrile

Chemical Property of (6Z,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2,6,10-trimethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6Z,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2,6,10-trimethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienenitrile

There total 1 articles about (6Z,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2,6,10-trimethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienenitrile 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) → (6Z,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2,6,10-trimethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienenitrile (193146-46-2)

Guidance literature:

Multi-step reaction with 14 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

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; acetonitrile; tert-butyl alcohol; pentane; benzene;

DOI:10.1021/ja971110h

Reference yield:

(6Z,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2,6,10-trimethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienenitrile (193146-46-2) → epothilone B (152044-54-7)

Guidance literature:

Multi-step reaction with 10 steps

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

2: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min

3: 96 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

4: 85 percent / camphorsulfonic acid / CH₂Cl₂; methanol / 0.5 h / 0 - 25 °C

5: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min, 2) CH₂Cl₂, -78 deg C -> 0 deg C, 30 min

6: 90 percent / NaClO₂, isobutylene, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 1 h / Ambient temperature

7: 73 percent / TBAF / tetrahydrofuran / 8 h / 25 °C

8: 1) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2) 4-DMAP / 1) THF, 25 deg C, 15 min, 2) toluene, 25 deg C, 12 h

9: 91 percent / CF₃CO₂H / CH₂Cl₂ / 1) -20 deg C -> 0 deg C, 2) 0 deg C, 1 h

10: Na₂EDTA, 1,1,1-trifluoroacetone, Oxone, NaHCO₃ / acetonitrile; H₂O / 0 °C

With 2,6-dimethylpyridine; dmap; Oxone; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; 1,1,1-trifluoro-2-propanone; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; edetate disodium; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; isobutene; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja971110h

Reference yield:

(6Z,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2,6,10-trimethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienenitrile (193146-46-2) → epothilone D (189453-10-9)

Guidance literature:

Multi-step reaction with 9 steps

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

2: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min

3: 96 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

4: 85 percent / camphorsulfonic acid / CH₂Cl₂; methanol / 0.5 h / 0 - 25 °C

5: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min, 2) CH₂Cl₂, -78 deg C -> 0 deg C, 30 min

6: 90 percent / NaClO₂, isobutylene, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 1 h / Ambient temperature

7: 73 percent / TBAF / tetrahydrofuran / 8 h / 25 °C

8: 1) Et₃N, 2,4,6-trichlorobenzoyl chloride, 2) 4-DMAP / 1) THF, 25 deg C, 15 min, 2) toluene, 25 deg C, 12 h

9: 91 percent / CF₃CO₂H / CH₂Cl₂ / 1) -20 deg C -> 0 deg C, 2) 0 deg C, 1 h

With 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; isobutene; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol;

DOI:10.1021/ja971110h

upstream raw materials:

ethyl 2-methylthiazole-4-carboxylate

Downstream raw materials:

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

(5S,8R,9S,10S,17S,Z)-9-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-2,2,3,3,6,6,8,10,14,19,19,20,20-tridecamethyl-17-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,18-dioxa-3,19-disilahenicos-14-en-7-one

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