(3S,4S)-3-Benzoyloxy-2-(2-bromoethyl)-4-(tert-butyldimethylsilyloxy)cyclohex-1-ene

Base Information

• Chemical Name: (3S,4S)-3-Benzoyloxy-2-(2-bromoethyl)-4-(tert-butyldimethylsilyloxy)cyclohex-1-ene
• CAS No.: 207788-97-4
• Molecular Formula: C₂₁H₃₁BrO₃Si
• Molecular Weight: 439.465
• Mol file: 207788-97-4.mol

Synonyms:(3S,4S)-3-Benzoyloxy-2-(2-bromoethyl)-4-(tert-butyldimethylsilyloxy)cyclohex-1-ene

Chemical Property of (3S,4S)-3-Benzoyloxy-2-(2-bromoethyl)-4-(tert-butyldimethylsilyloxy)cyclohex-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-Benzoyloxy-2-(2-bromoethyl)-4-(tert-butyldimethylsilyloxy)cyclohex-1-ene

There total 4 articles about (3S,4S)-3-Benzoyloxy-2-(2-bromoethyl)-4-(tert-butyldimethylsilyloxy)cyclohex-1-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: 84.7%

benzoic acid (65-85-0,8013-63-6) + (1R,6S)-2-(2-Bromoethyl)-6-(tert-butyldimethylsilyloxy)cyclohex-2-en-1-ol (207788-92-9) → (3S,4S)-3-Benzoyloxy-2-(2-bromoethyl)-4-(tert-butyldimethylsilyloxy)cyclohex-1-ene (207788-97-4)

Guidance literature:

With tributylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 16h; Ambient temperature;

DOI:10.1055/s-1998-5931

Reference yield:

(1S,2R)-3-(2-bromoethyl)cyclohex-5-ene-1,2-diol (164021-78-7) → (3S,4S)-3-Benzoyloxy-2-(2-bromoethyl)-4-(tert-butyldimethylsilyloxy)cyclohex-1-ene (207788-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / iPr₂NEt / CH₂Cl₂ / 1.) -78 deg C, 10 min, 2.) -78 deg C, 5 h; r.t., 20 h

2: 84.7 percent / DEAD, Bu₃P / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) r.t., 16 h

With tributylphosphine; N-ethyl-N,N-diisopropylamine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;

DOI:10.1135/cccc19990203

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (3S,4S)-3-Benzoyloxy-2-(2-bromoethyl)-4-(tert-butyldimethylsilyloxy)cyclohex-1-ene (207788-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: i-Pr₂NEt / CH₂Cl₂ / 1.) -78 deg C, 5 h, 2.) -78 deg C to r.t., 20 h

2: 84 percent / DEAD, Bu₃P / tetrahydrofuran / 16 h / Ambient temperature

With tributylphosphine; N-ethyl-N,N-diisopropylamine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-1998-5931

upstream raw materials:

benzoic acid

(1R,6S)-2-(2-Bromoethyl)-6-(tert-butyldimethylsilyloxy)cyclohex-2-en-1-ol

t-butyldimethylsiyl triflate

(1S,2R)-3-(2-bromoethyl)cyclohex-5-ene-1,2-diol

Downstream raw materials:

Benzoic acid (1S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-2-[2-(2-oxo-oxazol-3-yl)-ethyl]-cyclohex-2-enyl ester

3-<2-<(5S,6S)-6-Benzoyloxy-5-(tert-butyldimethylsilyloxy)cyclohex-1-enyl>ethyl><1,3>oxazolidine-2,4-dione

3-(2-(5S,6S)-6-Benzoyloxy-5-hydroxy-1-cyclohexenyl)ethyl<1,3>oxazolidine-2,4-dione

3-(2-(5S,6S)-5,6-Di(benzoyloxy)cyclohex-1-enyl)ethyl<1,3>oxazolidine-2,4-dione