4-[(1E,5E)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-6-trityloxymethyl-undeca-1,5-dienyl]-2-methyl-thiazole

Base Information

• Chemical Name: 4-[(1E,5E)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-6-trityloxymethyl-undeca-1,5-dienyl]-2-methyl-thiazole
• CAS No.: 226940-56-3
• Molecular Formula: C₄₉H₇₁NO₃SSi₂
• Molecular Weight: 810.345

Synonyms:4-[(1E,5E)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-6-trityloxymethyl-undeca-1,5-dienyl]-2-methyl-thiazole

Chemical Property of 4-[(1E,5E)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-6-trityloxymethyl-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,5E)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-6-trityloxymethyl-undeca-1,5-dienyl]-2-methyl-thiazole

There total 11 articles about 4-[(1E,5E)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-6-trityloxymethyl-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:

trityl chloride (76-83-5) + (2E,6E)-(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-[(S)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl]-6-methyl-7-(2-methyl-thiazol-4-yl)-hepta-2,6-dien-1-ol (226940-55-2) → 4-[(1E,5E)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-6-trityloxymethyl-undeca-1,5-dienyl]-2-methyl-thiazole (226940-56-3)

Guidance literature:

With dmap; In N,N-dimethyl-formamide; at 70 ℃; for 18h; Yield given;

DOI:10.1039/a809954e

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 4-[(1E,5E)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-6-trityloxymethyl-undeca-1,5-dienyl]-2-methyl-thiazole (226940-56-3)

Guidance literature:

Multi-step reaction with 11 steps

1: imidazole / dimethylformamide / 1 h / 0 - 25 °C

2: NaI / acetone / 12 h / Heating

3: 96 percent / Li₂CuCl₄ / tetrahydrofuran / 1 h / 0 °C

4: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

5: NaBH₄ / ethanol / 0.5 h / 0 °C

6: 100 percent / I₂, PPh₃ / acetonitrile; diethyl ether / 1 h / 0 - 25 °C

7: 2 h / 100 °C

8: KHMDS / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) -78 deg C, 3 h

9: benzene / 18 h / Heating

10: DIBAL-H / tetrahydrofuran / 3 h / -78 °C

11: DMAP / dimethylformamide / 18 h / 70 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; dilithium tetrachlorocuprate; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; triphenylphosphine; sodium iodide; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;

DOI:10.1039/a809954e

Reference yield:

(2R)-(tert-butyldimethyl)-(3-iodo-2-methylpropoxy)silane (105859-46-9) → 4-[(1E,5E)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,10-dimethyl-6-trityloxymethyl-undeca-1,5-dienyl]-2-methyl-thiazole (226940-56-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / Li₂CuCl₄ / tetrahydrofuran / 1 h / 0 °C

2: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

3: NaBH₄ / ethanol / 0.5 h / 0 °C

4: 100 percent / I₂, PPh₃ / acetonitrile; diethyl ether / 1 h / 0 - 25 °C

5: 2 h / 100 °C

6: KHMDS / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) -78 deg C, 3 h

7: benzene / 18 h / Heating

8: DIBAL-H / tetrahydrofuran / 3 h / -78 °C

9: DMAP / dimethylformamide / 18 h / 70 °C

With dmap; sodium tetrahydroborate; dilithium tetrachlorocuprate; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; triphenylphosphine; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1039/a809954e

upstream raw materials:

trityl chloride

(2E,6E)-(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-[(S)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl]-6-methyl-7-(2-methyl-thiazol-4-yl)-hepta-2,6-dien-1-ol

tert-butyldimethylsilyl chloride

(2R)-(tert-butyldimethyl)-(3-iodo-2-methylpropoxy)silane

Downstream raw materials:

(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2,10-dimethyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dien-1-ol

(12E,16E)-(3S,6R,7S,8S,15S)-1,3,15-Tris-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-12-trityloxymethyl-heptadeca-12,16-dien-5-one

(12E,16E)-(3S,6R,7S,8S,15S)-1,3,7,15-Tetrakis-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,16-pentamethyl-17-(2-methyl-thiazol-4-yl)-12-trityloxymethyl-heptadeca-12,16-dien-5-one

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

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