(S)-1-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)hex-5-ene

Base Information

• Chemical Name: (S)-1-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)hex-5-ene
• CAS No.: 1255639-72-5
• Molecular Formula: C₂₈H₄₄O₂Si₂
• Molecular Weight: 468.827
• Mol file: 1255639-72-5.mol

Synonyms:(S)-1-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)hex-5-ene

Chemical Property of (S)-1-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)hex-5-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)hex-5-ene

There total 4 articles about (S)-1-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)hex-5-ene 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: 90.0%

(3S)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-ol (127793-65-1) + tert-butylchlorodiphenylsilane (58479-61-1) → (S)-1-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)hex-5-ene (1255639-72-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 21h; Inert atmosphere;

DOI:10.1021/ml1001807

Reference yield:

3-(tert-butyldimethylsilanyloxy)propionaldehyde (89922-82-7) → (S)-1-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)hex-5-ene (1255639-72-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 0.08 h / 20 °C / Molecular sieve; Inert atmosphere

1.2: 139 h / -78 - -20 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 21 h / 20 °C / Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; In N,N-dimethyl-formamide; toluene; 1.1: Keck allylation / 1.2: Keck allylation;

DOI:10.1021/ml1001807

Reference yield:

3-tert-butyldimethylsilyloxy-1-propanol (73842-99-6) → (S)-1-(tert-butyldimethylsiloxy)-3-(tert-butyldiphenylsiloxy)hex-5-ene (1255639-72-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridinium chlorochromate / dichloromethane / 0 - 20 °C

2.1: C₄₆H₃₈O₇Ti₂ / dichloromethane / 0.17 h / 20 °C / Inert atmosphere; Molecular sieve

2.2: -78 - -20 °C / Inert atmosphere; Molecular sieve

3.1: 1H-imidazole; dmap / dichloromethane / Inert atmosphere

With 1H-imidazole; dmap; C₄₆H₃₈O₇Ti₂; pyridinium chlorochromate; In dichloromethane; 2.2: Keck allylation;

DOI:10.1055/s-0030-1260246

upstream raw materials:

3-(tert-butyldimethylsilanyloxy)propionaldehyde

(3S)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-ol

tert-butylchlorodiphenylsilane

3-tert-butyldimethylsilyloxy-1-propanol

Downstream raw materials:

(1E,3R,5S)-1-phenylocta-1,7-diene-3,5-diol

(4S,6R)-4-allyl-2,2-dimethyl-6-[(E)-2-phenylvinyl]-1,3-dioxane

(3S,5S)-5-(tert-butyldiphenylsiloxy)-1-phenyloct-7-en-1-yn-3-ol

C₃₇H₃₇NO₅Si