(R)-4,4-dibromo-2-methyl-1-(toluene-4-sulfonyloxy)but-3-ene

Base Information

• Chemical Name: (R)-4,4-dibromo-2-methyl-1-(toluene-4-sulfonyloxy)but-3-ene
• CAS No.: 868547-99-3
• Molecular Formula: C₁₂H₁₄Br₂O₃S
• Molecular Weight: 398.115
• Mol file: 868547-99-3.mol

Synonyms:(R)-4,4-dibromo-2-methyl-1-(toluene-4-sulfonyloxy)but-3-ene

Chemical Property of (R)-4,4-dibromo-2-methyl-1-(toluene-4-sulfonyloxy)but-3-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4,4-dibromo-2-methyl-1-(toluene-4-sulfonyloxy)but-3-ene

There total 5 articles about (R)-4,4-dibromo-2-methyl-1-(toluene-4-sulfonyloxy)but-3-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:

carbon tetrabromide (558-13-4) + (S)-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal (183293-41-6) → (R)-4,4-dibromo-2-methyl-1-(toluene-4-sulfonyloxy)but-3-ene (868547-99-3)

Guidance literature:

With 2,6-dimethylpyridine; triphenylphosphine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ol051711a

Reference yield:

(2S)-(+)-2-methyl-3-(toluene-4-sulfonyloxy)propionic acid methyl ester (84341-89-9) → (R)-4,4-dibromo-2-methyl-1-(toluene-4-sulfonyloxy)but-3-ene (868547-99-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DIBAL-H / toluene / 1.5 h / cooling

2.1: PPh₃ / CH₂Cl₂ / 0.17 h / cooling

2.2: 1.82 g / 2,6-lutidine / CH₂Cl₂ / 1 h / cooling

With diisobutylaluminium hydride; triphenylphosphine; In dichloromethane; toluene;

DOI:10.1016/j.tet.2006.05.019

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (R)-4,4-dibromo-2-methyl-1-(toluene-4-sulfonyloxy)but-3-ene (868547-99-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 0 - 20 °C

2: DIBAL-H / toluene / 1.5 h / -78 °C

3: PPh₃; 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; dmap; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In dichloromethane; toluene;

DOI:10.1021/ol051711a

upstream raw materials:

carbon tetrabromide

(S)-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal

(2S)-(+)-2-methyl-3-(toluene-4-sulfonyloxy)propionic acid methyl ester

p-toluenesulfonyl chloride

Downstream raw materials:

toluene-4-sulfonic acid (R)-2-methyl-4-triisopropylsilanylbut-3-ynyl ester

(4S)-3-[(2S,3R,5S)-2-allyl-3-hydroxy-5-methyl-7-triisopropylsilanylhept-6-ynoyl]-4-benzyloxazolidin-2-one