(S)-1,1-dibromo-5-(tert-butyldiphenylsilyloxy)-3-methyl-1-pentene

Base Information

• Chemical Name: (S)-1,1-dibromo-5-(tert-butyldiphenylsilyloxy)-3-methyl-1-pentene
• CAS No.: 270258-45-2
• Molecular Formula: C₂₂H₂₈Br₂OSi
• Molecular Weight: 496.357
• Mol file: 270258-45-2.mol

Synonyms:(S)-1,1-dibromo-5-(tert-butyldiphenylsilyloxy)-3-methyl-1-pentene

Chemical Property of (S)-1,1-dibromo-5-(tert-butyldiphenylsilyloxy)-3-methyl-1-pentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1,1-dibromo-5-(tert-butyldiphenylsilyloxy)-3-methyl-1-pentene

There total 5 articles about (S)-1,1-dibromo-5-(tert-butyldiphenylsilyloxy)-3-methyl-1-pentene 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:

carbon tetrabromide (558-13-4) + (2S, 3S)-5-(tert-butyldiphenylsilyloxy)-3-methylpentane-1,2-diol (187458-29-3) → (S)-1,1-dibromo-5-(tert-butyldiphenylsilyloxy)-3-methyl-1-pentene (270258-45-2)

Guidance literature:

With triphenylphosphine; In dichloromethane;

DOI:10.1039/a907910f

Reference yield:

(S)-2-methyl-4-(tert-butyldiphenylsilyloxy)butanol (169387-99-9) → (S)-1,1-dibromo-5-(tert-butyldiphenylsilyloxy)-3-methyl-1-pentene (270258-45-2)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -60 °C

2: PPh₃ / CH₂Cl₂ / 1.5 h / 20 °C

With oxalyl dichloride; dimethyl sulfoxide; triphenylphosphine; In dichloromethane; 1: Swern oxidation / 2: Wittig reaction;

DOI:10.1002/(sici)1099-0690(200003)2000:6<955::aid-ejoc955>3.0.co;2-y

Reference yield:

(3S)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyronitrile (188692-78-6) → (S)-1,1-dibromo-5-(tert-butyldiphenylsilyloxy)-3-methyl-1-pentene (270258-45-2)

Guidance literature:

Multi-step reaction with 6 steps

1: DIBAL-H / CH₂Cl₂

2: NaBH₄ / ethanol

3: 99 percent / imidazole / dimethylformamide

4: 86 percent / AcOH; H₂O / tetrahydrofuran

6: PPh₃ / CH₂Cl₂

With 1H-imidazole; sodium tetrahydroborate; water; diisobutylaluminium hydride; acetic acid; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: Reduction / 3: Substitution / 4: Hydrolysis / 5: Oxidation / 6: Addition;

DOI:10.1039/a907910f

upstream raw materials:

carbon tetrabromide

(2S, 3S)-5-(tert-butyldiphenylsilyloxy)-3-methylpentane-1,2-diol

tert-butylchlorodiphenylsilane

(S)-2-methyl-4-(tert-butyldiphenylsilyloxy)butanol

Downstream raw materials:

(S)-5-(tert-butyldiphenylsilyloxy)-3-methylpentyne

(S,E)-6-(tert-butyldiphenylsilyloxy)-3,4-dimethyl-2-hexen-1-ol

(S,E)-6-(tert-butyldiphenylsilyloxy)-1-chloro-3,4-dimethyl-2-hexene

(S,E)-6-(tert-butyldiphenylsilyloxy)-3,4-dimethyl-1-phenylsulfonyl-2-hexene