(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

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-dien-1-ol
• CAS No.: 488791-41-9
• Molecular Formula: C₃₅H₄₉NO₃SSi
• Molecular Weight: 591.93
• Mol file: 488791-41-9.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-dien-1-ol

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-dien-1-ol

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-dien-1-ol

There total 6 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-dien-1-ol 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: 72.0%

(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 (488791-39-5) → (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)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/ja028196l

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-dien-1-ol (488791-41-9)

Guidance literature:

Multi-step reaction with 4 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

With chromium dichloride; osmium(VIII) oxide; thionyl chloride; lithium triethylborohydride; 4-methylmorpholine N-oxide; nickel dichloride; In tetrahydrofuran; diethyl ether; 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-dien-1-ol (488791-41-9)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With thionyl chloride; lithium triethylborohydride; In tetrahydrofuran; diethyl ether; pentane;

DOI:10.1021/ja028196l

upstream raw materials:

(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

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

(E)-2-methyl-3-(2-methylthiazol-4-yl)acrylaldehyde

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)-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

(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

(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