(E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-7-methyl-octa-2,7-dien-4-ynal

Base Information

• Chemical Name: (E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-7-methyl-octa-2,7-dien-4-ynal
• CAS No.: 139057-31-1
• Molecular Formula: C₂₅H₂₈O₂Si
• Molecular Weight: 388.582
• Mol file: 139057-31-1.mol

Synonyms:(E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-7-methyl-octa-2,7-dien-4-ynal

Chemical Property of (E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-7-methyl-octa-2,7-dien-4-ynal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-7-methyl-octa-2,7-dien-4-ynal

There total 6 articles about (E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-7-methyl-octa-2,7-dien-4-ynal 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: 87.0%

(6R)-tert-Butyldiphenylsiloxy-7-methylocta-2,7-dien-4-yn-1-ol (139057-30-0) → (E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-7-methyl-octa-2,7-dien-4-ynal (139057-31-1)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1248/cpb.39.2545

Reference yield:

2-(tert-Butyldiphenylsiloxy)-3-methyl-but-3-enal (97971-47-6) → (E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-7-methyl-octa-2,7-dien-4-ynal (139057-31-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) Ph₃P, 2) zinc powder / 1) CH₂Cl₂, 5 min, 0 deg C, 2) 3 h, r.t.

2: 1) n-BuLi 2) water / 1) hexane, THF, a) -78 deg C, 1h, b) 25 deg C, 1 h, 2) r.t., 30 min

3: 1) n-BuLi / 1) hexane, THF, 2 h, -78 deg C, 2) 4 h, -78 deg C

4: 1) NaH / 1) benzene, 30 min, r.t., 2) benzene, 30 min, r.t.

5: 90 percent / i-Bu₂AlH / hexane; CH₂Cl₂ / 1 h / -78 °C

6: 87 percent / MnO₂ / CH₂Cl₂ / 0.5 h / Ambient temperature

With manganese(IV) oxide; n-butyllithium; water; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; zinc; In hexane; dichloromethane;

DOI:10.1248/cpb.39.2545

Reference yield:

(3R)-tert-Butyldiphenylsilyloxy-4-methylpent-4-en-1-yne (139057-27-5) → (E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-7-methyl-octa-2,7-dien-4-ynal (139057-31-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) n-BuLi / 1) hexane, THF, 2 h, -78 deg C, 2) 4 h, -78 deg C

2: 1) NaH / 1) benzene, 30 min, r.t., 2) benzene, 30 min, r.t.

3: 90 percent / i-Bu₂AlH / hexane; CH₂Cl₂ / 1 h / -78 °C

4: 87 percent / MnO₂ / CH₂Cl₂ / 0.5 h / Ambient temperature

With manganese(IV) oxide; n-butyllithium; sodium hydride; diisobutylaluminium hydride; In hexane; dichloromethane;

DOI:10.1248/cpb.39.2545

upstream raw materials:

(6R)-tert-Butyldiphenylsiloxy-7-methylocta-2,7-dien-4-yn-1-ol

2-(tert-Butyldiphenylsiloxy)-3-methyl-but-3-enal

(3R)-tert-Butyldiphenylsilyloxy-4-methylpent-4-en-1-yne

(4R)-tert-Butyldiphenylsilyloxy-5-methylhex-5-en-1-ynal

Downstream raw materials:

Methyl (8R)-tert-butyldiphenylsiloxy-9-methyldeca-(2E,4E),9-trien-6-ynoate