(5R,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-5-triisopropylsilanyloxy-dec-1-en-7-yne

Base Information

• Chemical Name: (5R,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-5-triisopropylsilanyloxy-dec-1-en-7-yne
• CAS No.: 907998-56-5
• Molecular Formula: C₂₅H₅₀O₂Si₂
• Molecular Weight: 438.842
• Mol file: 907998-56-5.mol

Synonyms:(5R,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-5-triisopropylsilanyloxy-dec-1-en-7-yne

Chemical Property of (5R,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-5-triisopropylsilanyloxy-dec-1-en-7-yne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-5-triisopropylsilanyloxy-dec-1-en-7-yne

There total 1 articles about (5R,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-5-triisopropylsilanyloxy-dec-1-en-7-yne 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: 97.0%

(5R,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-dec-1-en-7-yn-5-ol (907998-55-4) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (5R,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-5-triisopropylsilanyloxy-dec-1-en-7-yne (907998-56-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/ol061383u

Reference yield:

(5R,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-5-triisopropylsilanyloxy-dec-1-en-7-yne (907998-56-5) → (S)-3-[(R)-7-[(2S,5S)-5-[(4S,7R,Z)-2,2-diphenyl-7-[(2R,5R)-5-[(R)-1-[triisopropylsilyloxy]tridecyl]tetrahydrofuran-2-yl]-4,7-dihydro-1,3,2-dioxasilepin-4-yl]tetrahydrofuran-2-yl]-2-[triisopropylsilyloxy]hept-5-enyl]-5-methylfuran-2(5H)-one

Guidance literature:

Multi-step reaction with 4 steps

1.1: 96 percent / p-PTS / ethanol / 3 h / 50 °C

2.1: Red-Al / tetrahydrofuran; toluene / 0 - 20 °C

2.2: ethyl acetate / tetrahydrofuran; toluene / 0.17 h / 0 °C

2.3: 83 percent / iodine / tetrahydrofuran; toluene / 0.5 h / -78 - 20 °C

3.1: 84 percent / K₂CO₃; hydrazine / Pd(PPh₃)2Cl₂ / tetrahydrofuran / 48 h / 45 °C / 2327.17 Torr

4.1: second generation Grubbs catalyst / CH₂Cl₂ / 45 °C

With pyridinium p-toluenesulfonate; potassium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; hydrazine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/ol061383u

Reference yield:

(5R,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-5-triisopropylsilanyloxy-dec-1-en-7-yne (907998-56-5) → (S)-3-[(R,E)-6-[(1S,2S,6R,10S,Z)-4,4-diphenyl-6-[(2R,5R)-5-[(R)-1-[triisopropylsilyloxy]tridecyl]tetrahydrofuran-2-yl]-3,5,13-trioxa-4-sila-bicyclo[8.2.1]tridec-7-en-2-yl]-2-[triisopropylsilyloxy]hex-5-enyl]-5-methylfuran-2(5H)-one

Guidance literature:

Multi-step reaction with 4 steps

1.1: 96 percent / p-PTS / ethanol / 3 h / 50 °C

2.1: Red-Al / tetrahydrofuran; toluene / 0 - 20 °C

2.2: ethyl acetate / tetrahydrofuran; toluene / 0.17 h / 0 °C

2.3: 83 percent / iodine / tetrahydrofuran; toluene / 0.5 h / -78 - 20 °C

3.1: 84 percent / K₂CO₃; hydrazine / Pd(PPh₃)2Cl₂ / tetrahydrofuran / 48 h / 45 °C / 2327.17 Torr

4.1: second generation Grubbs catalyst / benzene / 10 h / 60 °C

With pyridinium p-toluenesulfonate; potassium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; hydrazine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; ethanol; toluene; benzene;

DOI:10.1021/ol061383u

upstream raw materials:

(5R,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-dec-1-en-7-yn-5-ol

triisopropylsilyl trifluoromethanesulfonate