4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: 4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 150618-06-7
• Molecular Formula: C₂₇H₃₇NO₆Si
• Molecular Weight: 499.679
• Mol file: 150618-06-7.mol

Synonyms:4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid 2-trimethylsilanyl-ethyl ester

Chemical Property of 4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid 2-trimethylsilanyl-ethyl ester

There total 1 articles about 4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid 2-trimethylsilanyl-ethyl 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: 90.0%

2-(Trimethylsilyl)ethanol (2916-68-9) + carbon monoxide (201230-82-2) + N-tert.-butoxycarbonyl-(4-trifluoromethanesulfonyloxy)-L-phenylalanine benzyl ester (123993-20-4) → 4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid 2-trimethylsilanyl-ethyl ester (150618-06-7)

Guidance literature:

With palladium diacetate; 1,3-bis-(diphenylphosphino)propane; triethylamine; In dimethyl sulfoxide; at 80 ℃; for 2h;

DOI:10.1016/S0960-894X(01)00269-4

Reference yield: 80.0%

4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid 2-trimethylsilanyl-ethyl ester (150618-06-7) → 4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid (150618-07-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1016/S0960-894X(01)00269-4

Reference yield:

4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid 2-trimethylsilanyl-ethyl ester (150618-06-7) → 3-[4-((S)-2-Amino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ5-phosphanylidene)-propionic acid methyl ester (460322-88-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / Bu₄NF / tetrahydrofuran / 5 h / 20 °C

2: 42 percent / EDC; DMAP / tetrahydrofuran / 28 h / 20 °C

3: H₂ / Pd/C / methanol / 0.5 h / 20 °C

4: TFA / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; tetrabutyl ammonium fluoride; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0960-894X(01)00269-4

upstream raw materials:

2-(Trimethylsilyl)ethanol

carbon monoxide

N-tert.-butoxycarbonyl-(4-trifluoromethanesulfonyloxy)-L-phenylalanine benzyl ester

Downstream raw materials:

4-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-benzoic acid

3-[4-((S)-2-Amino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid methyl ester

3-[4-((S)-2-Acetylamino-2-carboxy-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid methyl ester

3-[4-(2-benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid methyl ester