Glycine, N-[(1,1-diMethylethoxy)carbonyl]thio-L-phenylalanyl-, Methyl ester

Base Information

• Chemical Name: Glycine, N-[(1,1-diMethylethoxy)carbonyl]thio-L-phenylalanyl-, Methyl ester
• CAS No.: 128421-85-2
• Molecular Formula: C17H24N2O5S
• Molecular Weight: 352.455
• Mol file: 128421-85-2.mol

Synonyms:Glycine, N-[(1,1-diMethylethoxy)carbonyl]thio-L-phenylalanyl-, Methyl ester;Glycine, N-[(1,1-diMethylethoxy)carbonyl]thio-L-phenylalanyl-, Methyl ester-2

Chemical Property of Glycine, N-[(1,1-diMethylethoxy)carbonyl]thio-L-phenylalanyl-, Methyl ester

Chemical Property:

Purity/Quality:

≥95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Glycine, N-[(1,1-diMethylethoxy)carbonyl]thio-L-phenylalanyl-, Methyl ester

There total 1 articles about Glycine, N-[(1,1-diMethylethoxy)carbonyl]thio-L-phenylalanyl-, 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:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → methyl (S)-(2-((tert-butoxycarbonyl)amino)-3-phenylpropanethioyl)glycinate (128421-85-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

1.2: 24 h / 20 °C / Inert atmosphere

2.1: Lawessons reagent / toluene / 4 h / Reflux; Inert atmosphere

With Lawessons reagent; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In dichloromethane; toluene;

DOI:10.1021/jacs.5b03135

Reference yield: 96.0%

methyl (S)-(2-((tert-butoxycarbonyl)amino)-3-phenylpropanethioyl)glycinate (128421-85-2) → (S)-2-[2-(tert-butoxycarbonylamino)-3-phenylpropanethioamido]acetic acid

Guidance literature:

N-tert-butoxycarbonyl-L-thiophenylalanylglycine methyl ester; With sodium hydroxide; In methanol; water; at 0 - 20 ℃; for 16h; Inert atmosphere;

With potassium hydrogensulfate; In water; pH=1; Inert atmosphere;

DOI:10.1055/s-0031-1289594

Reference yield: 60.0%

methyl (S)-(2-((tert-butoxycarbonyl)amino)-3-phenylpropanethioyl)glycinate (128421-85-2) + N-succinimidyl 4-pentenoic acid ester (331754-32-6) → (N-(4-pentenoyl)-(thio)phenylalanyl)glycine methyl ester

Guidance literature:

methyl (S)-(2-((tert-butoxycarbonyl)amino)-3-phenylpropanethioyl)glycinate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 24h;

N-succinimidyl 4-pentenoic acid ester; With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

Boc-Phe-ψ(CH2NH)-Gly-OMe

(S)-2-[1-(tert-butoxycarbonylamino)-2-phenylethyl]thiazol-5-yl trifluoromethanesulfonate

tert-butyl N-[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]carbamate

H-PheΨGly-OMe