benzyl 5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-3-methylpentanoate

Base Information

• Chemical Name: benzyl 5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-3-methylpentanoate
• CAS No.: 1452161-94-2
• Molecular Formula: C₁₉H₃₂O₄Si
• Molecular Weight: 352.546
• Mol file: 1452161-94-2.mol

Synonyms:benzyl 5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-3-methylpentanoate

Chemical Property of benzyl 5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-3-methylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-3-methylpentanoate

There total 2 articles about benzyl 5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-3-methylpentanoate 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: 93.0%

Benzyl acetate (140-11-4) + 4-(tert-butyldimethylsilyloxy)butan-2-one (120591-36-8) → benzyl 5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-3-methylpentanoate (1452161-94-2)

Guidance literature:

Benzyl acetate; With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 ℃; for 0.5h;

4-(tert-butyldimethylsilyloxy)butan-2-one; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 ℃; for 1h;

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → benzyl 5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-3-methylpentanoate (1452161-94-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 20 °C

2.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.5 h / -78 °C

2.2: 1 h / -78 °C

With 1H-imidazole; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; N,N-dimethyl-formamide;

Reference yield: 64.0%

bis(trichloromethyl) carbonate (32315-10-9) + benzyl 5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-3-methylpentanoate (1452161-94-2) → benzyl 2-(4-methyl-2-oxo-1,3-dioxan-4-yl)acetate (1452161-93-1)

Guidance literature:

benzyl 5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-3-methylpentanoate; With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; for 24h;

bis(trichloromethyl) carbonate; With pyridine; In dichloromethane; at 0 ℃; for 0.5h;

upstream raw materials:

tert-butyldimethylsilyl chloride

Benzyl acetate

4-(tert-butyldimethylsilyloxy)butan-2-one

Downstream raw materials:

benzyl 2-(4-methyl-2-oxo-1,3-dioxan-4-yl)acetate

phenyl 2-(4-methyl-2-oxo-1,3-dioxan-4-yl)acetate

2-(4-methyl-2-oxo-1,3-dioxan-4-yl)-N-phenylacetamide

benzyl 3,5-dihydroxy-3-methylpentanoate

Refernces

• 1、 Kang, Soosung,Watanabe, Mizuki,Jacobs,Yamaguchi, Masaya,Dahesh, Samira,Nizet, Victor,Leyh, Thomas S.,Silverman, Richard B.. "Synthesis of mevalonate-and fluorinated mevalonate prodrugs and their in vitro human plasma stability". . p. 448 - 461. Retrieved 2016/10/19.