L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]glycylglycylglycyl-N-[(trimethylsilyl)meth yl]-, methyl ester

Base Information

• Chemical Name: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]glycylglycylglycyl-N-[(trimethylsilyl)meth yl]-, methyl ester
• CAS No.: 429685-03-0
• Molecular Formula: C25H40N4O7Si
• Molecular Weight: 536.701
• Mol file: 429685-03-0.mol

Synonyms:

Chemical Property of L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]glycylglycylglycyl-N-[(trimethylsilyl)meth yl]-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]glycylglycylglycyl-N-[(trimethylsilyl)meth yl]-, methyl ester

There total 4 articles about L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]glycylglycylglycyl-N-[(trimethylsilyl)meth yl]-, methyl 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: 53.0%

2-(aminoacetyl-trimethylsilanylmethyl-amino)-3-phenyl-propionic acid methyl ester (916049-47-3) + Boc-Gly-Gly-OH (31972-52-8) → 2-({2-[2-(2-tert-butoxycarbonylaminoacetylamino)acetylamino]acetyl}trimethylsilylmethylamino)-3-phenylpropionic acid methyl ester (429685-03-0)

Guidance literature:

With 2,4,6-trimethyl-pyridine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/ja064737l

Reference yield:

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) → 2-({2-[2-(2-tert-butoxycarbonylaminoacetylamino)acetylamino]acetyl}trimethylsilylmethylamino)-3-phenylpropionic acid methyl ester (429685-03-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / potassium iodide; potassium carbonate / dimethylformamide / 12 h / 90 °C

2: 3.2 g / CH₂Cl₂ / 12 h / 20 °C

3: aq. HCl / ethyl acetate / 0.5 h / 20 °C

4: 53 percent / HATU; 2,4,6-collidine / dimethylformamide / 16 h / 20 °C

With 2,4,6-trimethyl-pyridine; hydrogenchloride; potassium carbonate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium iodide; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja064737l

Reference yield:

(S)-(+)-methyl 2-<(trimethylsilyl)methyl>amino-3-phenylpropionate (220438-32-4) → 2-({2-[2-(2-tert-butoxycarbonylaminoacetylamino)acetylamino]acetyl}trimethylsilylmethylamino)-3-phenylpropionic acid methyl ester (429685-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 3.2 g / CH₂Cl₂ / 12 h / 20 °C

2: aq. HCl / ethyl acetate / 0.5 h / 20 °C

3: 53 percent / HATU; 2,4,6-collidine / dimethylformamide / 16 h / 20 °C

With 2,4,6-trimethyl-pyridine; hydrogenchloride; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja064737l

upstream raw materials:

2-(aminoacetyl-trimethylsilanylmethyl-amino)-3-phenyl-propionic acid methyl ester

Boc-Gly-Gly-OH

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

(S)-(+)-methyl 2-<(trimethylsilyl)methyl>amino-3-phenylpropionate

Refernces