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

Base Information

• Chemical Name: 1(RS_S)-[5-tert-butyldiphenylsiloxy-2-methyl-(2S,3Z)-3-pentenylsulfinyl]-benzene
• CAS No.: 628340-19-2
• Molecular Formula: C₂₈H₃₄O₂SSi
• Molecular Weight: 462.728
• Mol file: 628340-19-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 1(RS_S)-[5-tert-butyldiphenylsiloxy-2-methyl-(2S,3Z)-3-pentenylsulfinyl]-benzene 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: 78.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 4-methyl-5(RSS)-phenylsulfinyl-(Z,4S)-2-penten-1-ol (628340-20-5) → 1(RSS)-[5-tert-butyldiphenylsiloxy-2-methyl-(2S,3Z)-3-pentenylsulfinyl]-benzene (628340-19-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2003.08.024

Reference yield:

4-methyl-5-phenylsulfanyl-(Z,4S)-2-penten-1-ol (556834-59-4) → 1(RSS)-[5-tert-butyldiphenylsiloxy-2-methyl-(2S,3Z)-3-pentenylsulfinyl]-benzene (628340-19-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 1H-imidazole; sodium periodate; In methanol; dichloromethane;

DOI:10.1016/j.tetlet.2003.08.024

Reference yield:

methyl 4-methyl-5-phenylsulfanyl-(Z,4S)-2-pentenoate (556834-58-3) → 1(RSS)-[5-tert-butyldiphenylsiloxy-2-methyl-(2S,3Z)-3-pentenylsulfinyl]-benzene (628340-19-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / AlH₃ / diethyl ether / 2 h / 0 °C

2: 95 percent / NaIO₄ / aq. methanol / 16 h / 20 °C

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

With 1H-imidazole; aluminium hydride; sodium periodate; In methanol; diethyl ether; dichloromethane;

DOI:10.1016/j.tetlet.2003.08.024

upstream raw materials:

tert-butylchlorodiphenylsilane

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

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

methyl 4-methyl-5-phenylsulfanyl-(Z,4S)-2-pentenoate

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

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