(2S,4R)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (2S,4R)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentyl 4-methylbenzenesulfonate
• CAS No.: 273738-41-3
• Molecular Formula: C₃₀H₄₀O₄SSi
• Molecular Weight: 524.797
• Mol file: 273738-41-3.mol

Synonyms:(2S,4R)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentyl 4-methylbenzenesulfonate

Chemical Property of (2S,4R)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentyl 4-methylbenzenesulfonate

There total 4 articles about (2S,4R)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentyl 4-methylbenzenesulfonate 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%

p-toluenesulfonyl chloride (98-59-9) + (2S,4R)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentan-1-ol → (2S,4R)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentyl 4-methylbenzenesulfonate (273738-41-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/ol0058386

Reference yield:

(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate (90270-02-3,97937-36-5) → (2S,4R)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentyl 4-methylbenzenesulfonate (273738-41-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 6 h / 20 °C

2: 88 percent / K₂CO₃ / methanol; H₂O / Heating

3: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 4 h / 20 °C

With dmap; potassium carbonate; triethylamine; In methanol; dichloromethane; water; 1: Silylation / 2: Hydrolysis / 3: Tosylation;

DOI:10.1021/ol0058386

Reference yield:

(2S,4R)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentyl acetate (176900-63-3) → (2S,4R)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentyl 4-methylbenzenesulfonate (273738-41-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / K₂CO₃ / methanol; H₂O / Heating

2: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 4 h / 20 °C

With dmap; potassium carbonate; triethylamine; In methanol; dichloromethane; water; 1: Hydrolysis / 2: Tosylation;

DOI:10.1021/ol0058386

upstream raw materials:

p-toluenesulfonyl chloride

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

tert-butylchlorodiphenylsilane

(2S,4R)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentyl acetate

Downstream raw materials:

tert-butyl[(2R,4R)-2,4-dimethylhexyloxy]diphenylsilane

(2S,3S,4R,6R)-3-hydroxy-2,4,6-trimethyl-octanoic acid (1S,2R,4R)-1-((S)-1-carboxyethyl)-2,4-dimethyl-hexyl ester

Toluene-4-sulfonic acid (E)-(2R,6S,8R)-9-(tert-butyl-diphenyl-silanyloxy)-2,4,6,8-tetramethyl-non-3-enyl ester

Toluene-4-sulfonic acid (E)-(2S,6S,8R)-9-(tert-butyl-diphenyl-silanyloxy)-2,4,6,8-tetramethyl-non-3-enyl ester