(6Z,10E)-(2S,8S,9S)-9-(tert-Butoxy-diphenyl-silanyloxy)-2,6,8,10-tetramethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienal

Base Information

• Chemical Name: (6Z,10E)-(2S,8S,9S)-9-(tert-Butoxy-diphenyl-silanyloxy)-2,6,8,10-tetramethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienal
• CAS No.: 488791-43-1
• Molecular Formula: C₃₅H₄₇NO₃SSi
• Molecular Weight: 589.915
• Mol file: 488791-43-1.mol

Synonyms:(6Z,10E)-(2S,8S,9S)-9-(tert-Butoxy-diphenyl-silanyloxy)-2,6,8,10-tetramethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienal

Chemical Property of (6Z,10E)-(2S,8S,9S)-9-(tert-Butoxy-diphenyl-silanyloxy)-2,6,8,10-tetramethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6Z,10E)-(2S,8S,9S)-9-(tert-Butoxy-diphenyl-silanyloxy)-2,6,8,10-tetramethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienal

There total 7 articles about (6Z,10E)-(2S,8S,9S)-9-(tert-Butoxy-diphenyl-silanyloxy)-2,6,8,10-tetramethyl-11-(2-methyl-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: 82.0%

(6Z,10E)-(2S,8S,9S)-9-(tert-Butoxy-diphenyl-silanyloxy)-2,6,8,10-tetramethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dien-1-ol (488791-41-9) → (6Z,10E)-(2S,8S,9S)-9-(tert-Butoxy-diphenyl-silanyloxy)-2,6,8,10-tetramethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienal (488791-43-1)

Guidance literature:

With pyridinium chlorochromate;

DOI:10.1039/b312213c

Reference yield:

4-[(E)-(3S,4R)-3-(tert-Butoxy-diphenyl-silanyloxy)-2,4-dimethyl-hexa-1,5-dienyl]-2-methyl-thiazole (488791-34-0) → (6Z,10E)-(2S,8S,9S)-9-(tert-Butoxy-diphenyl-silanyloxy)-2,6,8,10-tetramethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienal (488791-43-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 4-methylmorpholine N-oxide; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 18 h / 0 - 25 °C

1.2: 82 percent / NaIO₄ / methanol; H₂O / 1 h / 20 °C

2.1: 75 percent / CrCl₂; NiCl₂ / dimethylformamide / 25 h / 0 - 20 °C

3.1: 85 percent / SOCl₂ / diethyl ether; pentane / 6 h / -78 - 20 °C

4.1: 72 percent / LiEt₃BH / tetrahydrofuran / -78 - 20 °C

5.1: 82 percent / pyridine; DMP / CH₂Cl₂ / 4 h / 0 °C

With pyridine; chromium dichloride; osmium(VIII) oxide; thionyl chloride; phthalic acid dimethyl ester; lithium triethylborohydride; 4-methylmorpholine N-oxide; nickel dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; pentane;

DOI:10.1021/ja028196l

Reference yield:

(S)-4-Benzyl-3-[(E)-(2S,8S,9S)-9-(tert-butoxy-diphenyl-silanyloxy)-7-hydroxy-2,8,10-trimethyl-6-methylene-11-(2-methyl-thiazol-4-yl)-undec-10-enoyl]-oxazolidin-2-one (488791-37-3) → (6Z,10E)-(2S,8S,9S)-9-(tert-Butoxy-diphenyl-silanyloxy)-2,6,8,10-tetramethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienal (488791-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / SOCl₂ / diethyl ether; pentane / 6 h / -78 - 20 °C

2: 72 percent / LiEt₃BH / tetrahydrofuran / -78 - 20 °C

3: 82 percent / pyridine; DMP / CH₂Cl₂ / 4 h / 0 °C

With pyridine; thionyl chloride; phthalic acid dimethyl ester; lithium triethylborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;

DOI:10.1021/ja028196l

upstream raw materials:

(6Z,10E)-(2S,8S,9S)-9-(tert-Butoxy-diphenyl-silanyloxy)-2,6,8,10-tetramethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dien-1-ol

4-[(E)-(3S,4R)-3-(tert-Butoxy-diphenyl-silanyloxy)-2,4-dimethyl-hexa-1,5-dienyl]-2-methyl-thiazole

(S)-4-Benzyl-3-[(E)-(2S,8S,9S)-9-(tert-butoxy-diphenyl-silanyloxy)-7-hydroxy-2,8,10-trimethyl-6-methylene-11-(2-methyl-thiazol-4-yl)-undec-10-enoyl]-oxazolidin-2-one

(S)-4-Benzyl-3-[(6E,10E)-(2S,8S,9S)-9-(tert-butoxy-diphenyl-silanyloxy)-6-chloromethyl-2,8,10-trimethyl-11-(2-methyl-thiazol-4-yl)-undeca-6,10-dienoyl]-oxazolidin-2-one

Downstream raw materials:

(12Z,16E)-(3S,6R,7S,8S,14S,15S)-15-(tert-Butoxy-diphenyl-silanyloxy)-1,3,7-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,12,14,16-heptamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-one

(12Z,16E)-(3S,6R,7S,8S,14S,15S)-15-(tert-Butoxy-diphenyl-silanyloxy)-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4,4,6,8,12,14,16-heptamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-one

(12Z,16E)-(3S,6R,7S,8S,14S,15S)-15-(tert-Butoxy-diphenyl-silanyloxy)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,4,6,8,12,14,16-heptamethyl-17-(2-methyl-thiazol-4-yl)-heptadeca-12,16-dien-5-one