Benzoic acid (1R,2R)-1-((S)-2-benzenesulfinyl-1-methyl-ethyl)-2-bromo-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester

Base Information

• Chemical Name: Benzoic acid (1R,2R)-1-((S)-2-benzenesulfinyl-1-methyl-ethyl)-2-bromo-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester
• CAS No.: 628340-21-6
• Molecular Formula: C₃₅H₃₉BrO₄SSi
• Molecular Weight: 663.748
• Mol file: 628340-21-6.mol

Synonyms:Benzoic acid (1R,2R)-1-((S)-2-benzenesulfinyl-1-methyl-ethyl)-2-bromo-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester

Chemical Property of Benzoic acid (1R,2R)-1-((S)-2-benzenesulfinyl-1-methyl-ethyl)-2-bromo-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1R,2R)-1-((S)-2-benzenesulfinyl-1-methyl-ethyl)-2-bromo-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester

There total 3 articles about Benzoic acid (1R,2R)-1-((S)-2-benzenesulfinyl-1-methyl-ethyl)-2-bromo-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester 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: 90.0%

benzoic acid (65-85-0,8013-63-6) + 2-bromo-1-tert-butyldiphenylsilyloxy-4-methyl-5(RSS)-phenylsulfinyl-(2R,3R,4S)-pentan-3-ol (628340-18-1) → Benzoic acid (1R,2R)-1-((S)-2-benzenesulfinyl-1-methyl-ethyl)-2-bromo-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester (628340-21-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2003.08.024

Reference yield:

4-methyl-5-phenylsulfanyl-(Z,4S)-2-penten-1-ol (556834-59-4) → Benzoic acid (1R,2R)-1-((S)-2-benzenesulfinyl-1-methyl-ethyl)-2-bromo-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester (628340-21-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / NaIO₄ / aq. methanol / 16 h / 20 °C

2: 78 percent / imidazole / CH₂Cl₂ / 3 h / 20 °C

3: 75 percent / N-bromosuccinimide; H₂O / toluene / 4 h / 20 °C

4: 90 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 20 °C

With 1H-imidazole; dmap; sodium periodate; N-Bromosuccinimide; water; dicyclohexyl-carbodiimide; In methanol; dichloromethane; toluene;

DOI:10.1016/j.tetlet.2003.08.024

Reference yield:

4-methyl-5(RSS)-phenylsulfinyl-(Z,4S)-2-penten-1-ol (628340-20-5) → Benzoic acid (1R,2R)-1-((S)-2-benzenesulfinyl-1-methyl-ethyl)-2-bromo-3-(tert-butyl-diphenyl-silanyloxy)-propyl ester (628340-21-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / imidazole / CH₂Cl₂ / 3 h / 20 °C

2: 75 percent / N-bromosuccinimide; H₂O / toluene / 4 h / 20 °C

3: 90 percent / DCC; DMAP / CH₂Cl₂ / 12 h / 20 °C

With 1H-imidazole; dmap; N-Bromosuccinimide; water; dicyclohexyl-carbodiimide; In dichloromethane; toluene;

DOI:10.1016/j.tetlet.2003.08.024

upstream raw materials:

benzoic acid

2-bromo-1-tert-butyldiphenylsilyloxy-4-methyl-5(RS_S)-phenylsulfinyl-(2R,3R,4S)-pentan-3-ol

4-methyl-5-phenylsulfanyl-(Z,4S)-2-penten-1-ol

4-methyl-5(RS_S)-phenylsulfinyl-(Z,4S)-2-penten-1-ol

Downstream raw materials:

3-benzoyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Benzoic acid (2S,3R,4R)-1-benzyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-pyrrolidin-3-yl ester

(2S,3R,4R)-3-Benzoyloxy-2-hydroxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Benzoic acid (1R,2S)-1-[(R)-1-bromo-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-3-phenylsulfanyl-3-(2,2,2-trifluoro-acetoxy)-propyl ester