N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline

Base Information

• Chemical Name: N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline
• CAS No.: 224951-66-0
• Molecular Formula: C₂₃H₃₄N₂O₅
• Molecular Weight: 418.533
• Mol file: 224951-66-0.mol

Synonyms:N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline

Chemical Property of N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline

There total 7 articles about N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline 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: 99.0%

N-(tert-butoxycarbonyl)-(S)-phenylalanyl-(2S,5R)-5-tert-butylproline benzyl ester (412303-26-5) → N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline (224951-66-0)

Guidance literature:

With hydrogen; 10percent Pd/C; In methanol; at 20 ℃; for 18h; under 760.051 Torr;

DOI:10.1021/ja012442w

Reference yield: 64.0%

N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline allyl ester (224951-63-7) → N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline (224951-66-0)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1021/jo990294a

Reference yield:

(2S,5R)-N-(tert-butyloxycarbonyl)-5-tert-butylproline (185142-15-8) → N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline (224951-66-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / DIEA / CH₂Cl₂ / 18 h / Heating

2: 99 percent / HCl(g) / CH₂Cl₂ / 2 h / 20 °C

3: 92 percent / BOP-Cl; DIEA / CH₂Cl₂

4: 99 percent / H₂ / 10percent Pd/C / methanol / 18 h / 20 °C / 760.05 Torr

With hydrogenchloride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; 10percent Pd/C; In methanol; dichloromethane;

DOI:10.1021/ja012442w

upstream raw materials:

N-(tert-butyloxycarbonyl)-(2S)-phenylalanyl-(2S,5R)-5-tert-butylproline allyl ester

N-(tert-butoxycarbonyl)-(S)-phenylalanyl-(2S,5R)-5-tert-butylproline benzyl ester

(2S,5R)-N-(tert-butyloxycarbonyl)-5-tert-butylproline

(2S,5R)-N-(tert-butoxycarbonyl)-5-tert-butylpropline benzyl ester

Refernces

• 1、 Halab, Liliane,Lubell, William D.. "Use of Steric Interactions to Control Peptide Turn Geometry. Synthesis of Type VI β-Turn Mimics with 5-tert-Butylproline". . p. 3312 - 3321. Retrieved 2007/10/03.