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

Base Information

• Chemical Name: 2-bromo-1-tert-butyldiphenylsilyloxy-4-methyl-5(RS_S)-phenylsulfinyl-(2R,3R,4S)-pentan-3-ol
• CAS No.: 628340-18-1
• Molecular Formula: C₂₈H₃₅BrO₃SSi
• Molecular Weight: 559.64

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

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

Chemical Property:

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

There total 3 articles about 2-bromo-1-tert-butyldiphenylsilyloxy-4-methyl-5(RS_S)-phenylsulfinyl-(2R,3R,4S)-pentan-3-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: 75.0%

1(RSS)-[5-tert-butyldiphenylsiloxy-2-methyl-(2S,3Z)-3-pentenylsulfinyl]-benzene (628340-19-2) → 2-bromo-1-tert-butyldiphenylsilyloxy-4-methyl-5(RSS)-phenylsulfinyl-(2R,3R,4S)-pentan-3-ol (628340-18-1)

Guidance literature:

With N-Bromosuccinimide; water; In toluene; at 20 ℃; for 4h;

DOI:10.1016/j.tetlet.2003.08.024

Reference yield:

4-methyl-5-phenylsulfanyl-(Z,4S)-2-penten-1-ol (556834-59-4) → 2-bromo-1-tert-butyldiphenylsilyloxy-4-methyl-5(RSS)-phenylsulfinyl-(2R,3R,4S)-pentan-3-ol (628340-18-1)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; sodium periodate; N-Bromosuccinimide; water; 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) → 2-bromo-1-tert-butyldiphenylsilyloxy-4-methyl-5(RSS)-phenylsulfinyl-(2R,3R,4S)-pentan-3-ol (628340-18-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1016/j.tetlet.2003.08.024

upstream raw materials:

1(RS_S)-[5-tert-butyldiphenylsiloxy-2-methyl-(2S,3Z)-3-pentenylsulfinyl]-benzene

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:

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

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

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