tert-butyl (4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-hexanoate

Base Information

• Chemical Name: tert-butyl (4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-hexanoate
• CAS No.: 668436-17-7
• Molecular Formula: C₂₁H₃₃NO₅
• Molecular Weight: 379.497
• Mol file: 668436-17-7.mol

Synonyms:tert-butyl (4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-hexanoate

Chemical Property of tert-butyl (4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-hexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-hexanoate

There total 6 articles about tert-butyl (4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-hexanoate 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: 81.0%

tert-butyl (4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-(E)-2-hexenoate (488760-74-3) → tert-butyl (4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-hexanoate (668436-17-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1021/jm031022+

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester (51987-73-6) → tert-butyl (4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-hexanoate (668436-17-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 72 percent / LDA / tetrahydrofuran / -78 °C

2: 72 percent / Et₃N / 0 °C

3: 81 percent / LiAlH(O-t-Bu)3 / ethanol / -78 °C

4: H₂ / Pd/C / ethyl acetate / 4 h

With hydrogen; lithium tri-t-butoxyaluminum hydride; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; ethyl acetate; 2: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jo0486948

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → tert-butyl (4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-hexanoate (668436-17-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: K₂CO₃ / dimethylformamide / 1 h / 20 °C

1.2: 40 percent / dimethylformamide / 5 h / 20 °C

2.1: 81 percent / LiAlH(O-t-Bu)3 / ethanol / -78 °C

3.1: H₂ / Pd/C / ethyl acetate / 4 h

With hydrogen; potassium carbonate; lithium tri-t-butoxyaluminum hydride; palladium on activated charcoal; In ethanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo0486948

upstream raw materials:

tert-butyl (4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-(E)-2-hexenoate

bromoacetic acid tert-butyl ester

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

dimethyl [(3S)-4-phenyl-3-[N-(tert-butyloxycarbonyl)amino]-2-oxobutyl]phosphonate

Downstream raw materials:

(4R)-4-{1-[(S)-(tert-butoxycarbonyl)amino]-2-phenylethyl}-γ-butyrolactone