(R)-1-(tert-butyldimethylsilyl)oxy-2-methyl-5-benzyloxypentane

Base Information

• Chemical Name: (R)-1-(tert-butyldimethylsilyl)oxy-2-methyl-5-benzyloxypentane
• CAS No.: 329913-80-6
• Molecular Formula: C₁₉H₃₄O₂Si
• Molecular Weight: 322.563
• Mol file: 329913-80-6.mol

Synonyms:(R)-1-(tert-butyldimethylsilyl)oxy-2-methyl-5-benzyloxypentane

Chemical Property of (R)-1-(tert-butyldimethylsilyl)oxy-2-methyl-5-benzyloxypentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-(tert-butyldimethylsilyl)oxy-2-methyl-5-benzyloxypentane

There total 4 articles about (R)-1-(tert-butyldimethylsilyl)oxy-2-methyl-5-benzyloxypentane 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: 87.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + (R)-S75-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol (143728-66-9) → (R)-1-(tert-butyldimethylsilyl)oxy-2-methyl-5-benzyloxypentane (329913-80-6)

Guidance literature:

With triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1021/jo0056951

Reference yield:

(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal (104701-87-3) → (R)-1-(tert-butyldimethylsilyl)oxy-2-methyl-5-benzyloxypentane (329913-80-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / LiCl; DBU / acetonitrile / 2 h

2: 98 percent / H₂ / Pd/C / ethyl acetate / 20 h

3: 92 percent / DIBAL-H / various solvent(s) / 2 h / 20 °C

4: 87 percent / TESOTf / CH₂Cl₂ / 3 h / 0 °C

With hydrogen; triethylsilyl trifluoromethyl sulfonate; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; palladium on activated charcoal; In dichloromethane; ethyl acetate; acetonitrile; 1: Horner-Emmons condensation;

DOI:10.1021/jo0056951

Reference yield:

(R,E)-ethyl 5-(tert-butyldimethylsilyl)oxy-4-methyl-2-pentenoate (135212-08-7) → (R)-1-(tert-butyldimethylsilyl)oxy-2-methyl-5-benzyloxypentane (329913-80-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / H₂ / Pd/C / ethyl acetate / 20 h

2: 92 percent / DIBAL-H / various solvent(s) / 2 h / 20 °C

3: 87 percent / TESOTf / CH₂Cl₂ / 3 h / 0 °C

With hydrogen; triethylsilyl trifluoromethyl sulfonate; diisobutylaluminium hydride; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/jo0056951

upstream raw materials:

O-benzyl 2,2,2-trichloroacetimidate

(R)-S₇₅-((tert-butyldimethylsilyl)oxy)-4-methylpentan-1-ol

(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal

(R,E)-ethyl 5-(tert-butyldimethylsilyl)oxy-4-methyl-2-pentenoate

Downstream raw materials:

(2R)-5-benzyloxy-2-methyl-1-pentanal

(2R)-5-(benzyloxy)-2-methylpentan-1-ol