tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-7-hydroxy-4-oxo-(E)-2-heptenoate

Base Information

• Chemical Name: tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-7-hydroxy-4-oxo-(E)-2-heptenoate
• CAS No.: 768395-82-0
• Molecular Formula: C₁₆H₂₇NO₆
• Molecular Weight: 329.393
• Mol file: 768395-82-0.mol

Synonyms:tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-7-hydroxy-4-oxo-(E)-2-heptenoate

Chemical Property of tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-7-hydroxy-4-oxo-(E)-2-heptenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-7-hydroxy-4-oxo-(E)-2-heptenoate

There total 2 articles about tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-7-hydroxy-4-oxo-(E)-2-heptenoate 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: 53.0%

tert-butyl glyoxylate (7633-32-1) + dimethyl [(3S)-3-[N-(tert-butoxycarbonyl)amino]-5-hydroxy-2-oxopentyl]phosphonate (768395-80-8) → tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-7-hydroxy-4-oxo-(E)-2-heptenoate (768395-82-0)

Guidance literature:

With triethylamine; lithium chloride; In acetonitrile; at 0 ℃; for 1h;

DOI:10.1021/jm040780c

Reference yield:

tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate (40856-59-5,132957-40-5) → tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-7-hydroxy-4-oxo-(E)-2-heptenoate (768395-82-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 48 percent / hexane; tetrahydrofuran / 1 h / -78 °C

2.1: 53 percent / lithium chloride; triethylamine / acetonitrile / 1 h / 0 °C

With n-butyllithium; triethylamine; lithium chloride; In tetrahydrofuran; hexane; acetonitrile; 2.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jm040780c

Reference yield:

tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-7-hydroxy-4-oxo-(E)-2-heptenoate (768395-82-0) → 3-amino-4-oxo-heptanedioic acid 1-benzyl ester (768395-72-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 59 percent / H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

2.1: 62 percent / pyridinium dichromate / dimethylformamide / 2.5 h

3.1: aq. Cs₂CO₃ / methanol / pH 8

3.2: 72 percent / dimethylformamide / 6 h / 20 °C

4.1: 97 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

With dipyridinium dichromate; hydrogen; caesium carbonate; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm040780c

upstream raw materials:

tert-butyl glyoxylate

dimethyl [(3S)-3-[N-(tert-butoxycarbonyl)amino]-5-hydroxy-2-oxopentyl]phosphonate

tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate

Downstream raw materials:

3-amino-4-oxo-heptanedioic acid 1-benzyl ester

benzyl (3R/S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoate