(S)-2-bromo-7-(tert-butyldiphenylsilanyloxy)-hept-1-en-4-ol

Base Information

• Chemical Name: (S)-2-bromo-7-(tert-butyldiphenylsilanyloxy)-hept-1-en-4-ol
• CAS No.: 871355-29-2
• Molecular Formula: C₂₃H₃₁BrO₂Si
• Molecular Weight: 447.487
• Mol file: 871355-29-2.mol

Synonyms:(S)-2-bromo-7-(tert-butyldiphenylsilanyloxy)-hept-1-en-4-ol

Chemical Property of (S)-2-bromo-7-(tert-butyldiphenylsilanyloxy)-hept-1-en-4-ol

Chemical Property:

Purity/Quality:

95%-98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-bromo-7-(tert-butyldiphenylsilanyloxy)-hept-1-en-4-ol

There total 3 articles about (S)-2-bromo-7-(tert-butyldiphenylsilanyloxy)-hept-1-en-4-ol 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: 43.0%

C23H31BrO2Si (871355-14-5) → (S)-2-bromo-7-(tert-butyldiphenylsilanyloxy)-hept-1-en-4-ol (871355-29-2) + (R)-2-bromo-7-(tert-butyldiphenylsilanyloxy)-hept-1-en-4-ol (784194-08-7)

Guidance literature:

With Chiralpak-OD; chemoselective reaction; Resolution of racemate;

DOI:10.1055/s-0032-1317920

Reference yield:

4-((tert-butyldiphenylsilyl)oxy)butanal (127793-62-8) + 2-bromoallyl bromide (513-31-5) → (S)-2-bromo-7-(tert-butyldiphenylsilanyloxy)-hept-1-en-4-ol (871355-29-2) + (R)-2-bromo-7-(tert-butyldiphenylsilanyloxy)-hept-1-en-4-ol (784194-08-7)

Guidance literature:

4-((tert-butyldiphenylsilyl)oxy)butanal; 2-bromoallyl bromide; With iron(III) 2,2,6,6-tetramethyl-3,5-heptadionate; chromium(III) bromide; [2-(4-t-Bu-4,5-dihydrooxazol-2-yl)phenyl]-NH-SO₂-CH₂-Ph; manganese; triethylamine; In tetrahydrofuran; at 0 ℃; for 20h;

With acetic acid; In tetrahydrofuran; for 1h; Title compound not separated from byproducts;

DOI:10.1021/ja045557j

Reference yield:

C7H13BrO2 (871348-26-4) → (S)-2-bromo-7-(tert-butyldiphenylsilanyloxy)-hept-1-en-4-ol (871355-29-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 15 °C

2: Chiralpak-OD / Resolution of racemate

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1055/s-0032-1317920

upstream raw materials:

4-((tert-butyldiphenylsilyl)oxy)butanal

2-bromoallyl bromide

C₂₃H₃₁BrO₂Si

C₇H₁₃BrO₂

Downstream raw materials:

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

C₄₆H₇₁NO₈SSi₂

C₃₉H₆₃NO₅Si₂

C₃₉H₆₃NO₅Si₂