(E)-(S)-2-tert-Butoxycarbonylamino-6-oxo-dec-4-enoic acid benzyl ester

Base Information

• Chemical Name: (E)-(S)-2-tert-Butoxycarbonylamino-6-oxo-dec-4-enoic acid benzyl ester
• CAS No.: 474766-44-4
• Molecular Formula: C₂₂H₃₁NO₅
• Molecular Weight: 389.492
• Mol file: 474766-44-4.mol

Synonyms:(E)-(S)-2-tert-Butoxycarbonylamino-6-oxo-dec-4-enoic acid benzyl ester

Chemical Property of (E)-(S)-2-tert-Butoxycarbonylamino-6-oxo-dec-4-enoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-2-tert-Butoxycarbonylamino-6-oxo-dec-4-enoic acid benzyl ester

There total 3 articles about (E)-(S)-2-tert-Butoxycarbonylamino-6-oxo-dec-4-enoic acid benzyl ester 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: 77.0%

2-oxohexylphosphonic acid dimethyl ester (61728-15-2) + (S)-benzyl-4-oxo-2-<<(1,1-dimethylethoxy)carbonyl>amino>butanoate (124994-66-7) → (E)-(S)-2-tert-Butoxycarbonylamino-6-oxo-dec-4-enoic acid benzyl ester (474766-44-4)

Guidance literature:

With caesium carbonate; In acetonitrile; at 20 ℃; for 0.583333h;

DOI:10.1016/S0040-4039(02)01495-8

Reference yield:

2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester (30925-18-9) → (E)-(S)-2-tert-Butoxycarbonylamino-6-oxo-dec-4-enoic acid benzyl ester (474766-44-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-methylmorpholine; isobutyl chloroformate / tetrahydrofuran / 0.25 h / 0 °C

1.2: 69 percent / NaBH₄ / methanol / 1 h / 0 °C

2.1: 79 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.58 h / 0 °C

3.1: 77 percent / Cs₂CO₃ / acetonitrile / 0.58 h / 20 °C

With 4-methyl-morpholine; caesium carbonate; Dess-Martin periodane; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; acetonitrile; 2.1: Dess-Martin oxidation / 3.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/S0040-4039(02)01495-8

Reference yield:

(S)-benzyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate (105183-60-6) → (E)-(S)-2-tert-Butoxycarbonylamino-6-oxo-dec-4-enoic acid benzyl ester (474766-44-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.58 h / 0 °C

2: 77 percent / Cs₂CO₃ / acetonitrile / 0.58 h / 20 °C

With caesium carbonate; Dess-Martin periodane; In dichloromethane; acetonitrile; 1: Dess-Martin oxidation / 2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/S0040-4039(02)01495-8

upstream raw materials:

2-oxohexylphosphonic acid dimethyl ester

(S)-benzyl-4-oxo-2-<<(1,1-dimethylethoxy)carbonyl>amino>butanoate

2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester

(S)-benzyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate