(2S,3S)-2-(tert-butyldiphenylsilyl)oxy-3-methylpentanoic acid

Base Information

• Chemical Name: (2S,3S)-2-(tert-butyldiphenylsilyl)oxy-3-methylpentanoic acid
• CAS No.: 104855-39-2
• Molecular Formula: C₂₂H₃₀O₃Si
• Molecular Weight: 370.564
• Mol file: 104855-39-2.mol

Synonyms:(2S,3S)-2-(tert-butyldiphenylsilyl)oxy-3-methylpentanoic acid

Chemical Property of (2S,3S)-2-(tert-butyldiphenylsilyl)oxy-3-methylpentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-(tert-butyldiphenylsilyl)oxy-3-methylpentanoic acid

There total 7 articles about (2S,3S)-2-(tert-butyldiphenylsilyl)oxy-3-methylpentanoic acid 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: 75.0%

Benzyl (2S)-(tert-butyldiphenylsilyloxy)-(3S)-methylpentanoate (104881-82-5) → (2S,3S)-2-(tert-butyldiphenylsilyl)oxy-3-methylpentanoic acid (104855-39-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 2h;

DOI:10.1248/cpb.39.2545

Reference yield:

L-isoleucine (73-32-5,959215-79-3,18875-42-8) → (2S,3S)-2-(tert-butyldiphenylsilyl)oxy-3-methylpentanoic acid (104855-39-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaNO₂; acetic acid / H₂O

1.2: K₂CO₃ / methanol; H₂O

2.1: DBU / acetonitrile

3.1: imidazole / dimethylformamide

4.1: H₂ / Pd/C / ethanol

With 1H-imidazole; hydrogen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium nitrite; palladium on activated charcoal; In ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1271/bbb.68.1097

Reference yield:

(S)-2-Hydroxy-(S)-3-methylpentanoic acid benzyl ester (40297-93-6,113956-82-4,104855-41-6) → (2S,3S)-2-(tert-butyldiphenylsilyl)oxy-3-methylpentanoic acid (104855-39-2)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide

2: H₂ / Pd/C / ethanol

With 1H-imidazole; hydrogen; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1271/bbb.68.1097

upstream raw materials:

Benzyl (2S)-(tert-butyldiphenylsilyloxy)-(3S)-methylpentanoate

L-isoleucine

(2S,3S)-2-Hydroxy-3-methylpentanoic acid

(S)-2-Hydroxy-(S)-3-methylpentanoic acid benzyl ester

Downstream raw materials:

Methyl (9S),10-Epoxy-(8R)-((2'S)-tert-butyldiphenylsilyloxy-(3'S)-methylpentanoyloxy)-9-methyl-deca-(E,E,E)-trienoate

(2E,4E,6E)-(R)-8-[(2S,3S)-2-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentanoyloxy]-8-((R)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid methyl ester

AF-toxin II_c

(2E,4E,6E)-(R)-8-[(2S,3S)-2-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentanoyloxy]-8-((S)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid