(-)-(1R,2Z)-1-[tert-butyl(dimethyl)silanyl]-but-2-enyl pentafluorobenzoate

Base Information

• Chemical Name: (-)-(1R,2Z)-1-[tert-butyl(dimethyl)silanyl]-but-2-enyl pentafluorobenzoate
• CAS No.: 934242-93-0
• Molecular Formula: C₁₇H₂₁F₅O₂Si
• Molecular Weight: 380.43
• Mol file: 934242-93-0.mol

Synonyms:(-)-(1R,2Z)-1-[tert-butyl(dimethyl)silanyl]-but-2-enyl pentafluorobenzoate

Chemical Property of (-)-(1R,2Z)-1-[tert-butyl(dimethyl)silanyl]-but-2-enyl pentafluorobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1R,2Z)-1-[tert-butyl(dimethyl)silanyl]-but-2-enyl pentafluorobenzoate

There total 2 articles about (-)-(1R,2Z)-1-[tert-butyl(dimethyl)silanyl]-but-2-enyl pentafluorobenzoate 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:

pentafluorobenzoylchloride (2251-50-5) + 1-[tert-butyl(dimethyl)silanyl]but-2-yn-1-one (80594-40-7) → (-)-(1R,2Z)-1-[tert-butyl(dimethyl)silanyl]-but-2-enyl pentafluorobenzoate (934242-93-0) + (1S,2Z)-1-[tert-butyl(dimethyl)silanyl]-but-2-enyl pentafluorobenzoate

Guidance literature:

1-[tert-butyl(dimethyl)silanyl]but-2-yn-1-one; With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -30 ℃; for 0.5h;

With hydrogen; Lindlar's catalyst; In ethyl acetate; at 20 ℃; for 1h;

pentafluorobenzoylchloride; With pyridine; dmap; In diethyl ether; at 0 ℃; for 1h; Further stages.;

DOI:10.1021/ol063097o

Reference yield:

1-[tert-butyl(dimethyl)silanyl]but-2-yn-1-ol (301664-44-8) → (-)-(1R,2Z)-1-[tert-butyl(dimethyl)silanyl]-but-2-enyl pentafluorobenzoate (934242-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 87 percent / CrO₃; H₂SO₄ / acetone / 1 h / 20 °C

2.1: (R)-2-methyl-CBS-oxazaborolidine; BH₃*Me₂S / tetrahydrofuran; toluene / 0.5 h / -30 °C

2.2: H₂ / Lindlar catalyst / ethyl acetate / 1 h / 20 °C

2.3: DMAP; pyridine / diethyl ether / 1 h / 0 °C

With chromium(VI) oxide; dimethylsulfide borane complex; sulfuric acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; acetone; toluene; 1.1: Jones oxidation;

DOI:10.1021/ol063097o

Reference yield:

(-)-(1R,2Z)-1-[tert-butyl(dimethyl)silanyl]-but-2-enyl pentafluorobenzoate (934242-93-0) + diphenylzinc (1078-58-6) → (-)-(3S,1E)-[tert-butyl(dimethyl)(3-phenyl-but-1-enyl)]silane (934243-02-4)

Guidance literature:

diphenylzinc; With CuCN*2LiCl; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; at -30 ℃; for 0.75h;

(-)-(1R,2Z)-1-[tert-butyl(dimethyl)silanyl]-but-2-enyl pentafluorobenzoate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; at -30 ℃; for 24h; Further stages.;

DOI:10.1021/ol063097o

upstream raw materials:

pentafluorobenzoylchloride

1-[tert-butyl(dimethyl)silanyl]but-2-yn-1-one

1-[tert-butyl(dimethyl)silanyl]but-2-yn-1-ol

Downstream raw materials:

(-)-(3S,1E)-[tert-butyl(dimethyl)(3-phenyl-but-1-enyl)]silane

(S)-2-methyl-4-phenyl-1-butyric acid

(R)-(-)-2-methyl-4-phenylbutyric acid