(2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-2,4-dimethylpentyl phenyl sulfone

Base Information

• Chemical Name: (2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-2,4-dimethylpentyl phenyl sulfone
• CAS No.: 197016-00-5
• Molecular Formula: C₁₉H₃₄O₃SSi
• Molecular Weight: 370.629
• Mol file: 197016-00-5.mol

Synonyms:(2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-2,4-dimethylpentyl phenyl sulfone

Chemical Property of (2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-2,4-dimethylpentyl phenyl sulfone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-2,4-dimethylpentyl phenyl sulfone

There total 6 articles about (2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-2,4-dimethylpentyl phenyl sulfone 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: 99.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,4R)-5-phenylsulfonyl-2,4-dimethyl-pentan-1-ol (197016-08-3) → (2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-2,4-dimethylpentyl phenyl sulfone (197016-00-5)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 50 ℃;

DOI:10.1002/anie.199717451

Reference yield:

(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate (90270-02-3,97937-36-5) → (2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-2,4-dimethylpentyl phenyl sulfone (197016-00-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / I₂; Ph₃P; 1H-imidazole / tetrahydrofuran / 12 h

2: 91 percent / poly(ethylene glycol)-400 / 2.5 h / 130 °C

3: 91 percent / K₂CO₃ / methanol; H₂O / 12 h

4: 99 percent / DMAP; 1H-imidazole / tetrahydrofuran / 12 h

With 1H-imidazole; dmap; poly(ethylene glycol)-400; iodine; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; water;

DOI:10.1002/hlca.200290020

Reference yield:

(2S,4R)-5-iodo-2,4-dimethylpentan-1-ol acetate (197016-06-1) → (2R,4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-2,4-dimethylpentyl phenyl sulfone (197016-00-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / poly(ethylene glycol)-400 / 2.5 h / 130 °C

2: 91 percent / K₂CO₃ / methanol; H₂O / 12 h

3: 99 percent / DMAP; 1H-imidazole / tetrahydrofuran / 12 h

With 1H-imidazole; dmap; poly(ethylene glycol)-400; potassium carbonate; In tetrahydrofuran; methanol; water;

DOI:10.1002/hlca.200290020

upstream raw materials:

tert-butyldimethylsilyl chloride

(2S,4R)-5-phenylsulfonyl-2,4-dimethyl-pentan-1-ol

sodium benzenesulfonate

(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate

Downstream raw materials:

(3S,5R,8R,10S)-6-Acetoxy-7-benzenesulfonyl-11-(tert-butyl-dimethyl-silanyloxy)-3,5,8,10-tetramethyl-undecanoic acid methyl ester

(3S,5R,8R,10S)-7-Benzenesulfonyl-11-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-3,5,8,10-tetramethyl-undecanoic acid methyl ester