tert-Butoxycarbonyl-phenylalanyl-methionine methyl ester

Base Information

• Chemical Name: tert-Butoxycarbonyl-phenylalanyl-methionine methyl ester
• CAS No.: 40290-63-9
• Molecular Formula: C20H30N2O5S
• Molecular Weight: 410.535
• DSSTox Substance ID: DTXSID50193299
• Nikkaji Number: J623.692H
• Wikidata: Q83066017
• Mol file: 40290-63-9.mol

Synonyms:Boc-FM-OMe;Boc-Phe-Met-OMe;tert-butoxycarbonyl-phenylalanyl-methionine methyl ester

Chemical Property of tert-Butoxycarbonyl-phenylalanyl-methionine methyl ester

Chemical Property:

• Vapor Pressure: 1.2E-14mmHg at 25°C
• Boiling Point: 606.3°C at 760 mmHg
• Flash Point: 320.5°C
• PSA: 126.01000
• Density: 1.15g/cm³
• LogP: 3.57800
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 410.18754324
• Heavy Atom Count: 28
• Complexity: 515

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C(=O)NC(CCSC)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCSC)C(=O)OC

Technology Process of tert-Butoxycarbonyl-phenylalanyl-methionine methyl ester

There total 12 articles about tert-Butoxycarbonyl-phenylalanyl-methionine 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: 99.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride (2491-18-1) → Methyl ester of N-t-butyloxycarbonyl-L-phenylalanyl-L-methionine (40290-63-9)

Guidance literature:

With 2,6-dimethylpyridine; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; In water; at 20 ℃; for 1h; Green chemistry;

DOI:10.1021/acs.orglett.5b01812

Reference yield: 95.0%

Met-OMe (10332-17-9,874219-77-9) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → Methyl ester of N-t-butyloxycarbonyl-L-phenylalanyl-L-methionine (40290-63-9)

Guidance literature:

With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 2.5h;

DOI:10.1039/b709854e

Reference yield: 90.2%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + s-methionine hydrochloride (6810-12-4) → Methyl ester of N-t-butyloxycarbonyl-L-phenylalanyl-L-methionine (40290-63-9)

Guidance literature:

With O-Benzotriazol-1-yl-N,N,N',N'-bis(tetramethylene)uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 0.25h; Ambient temperature;

DOI:10.1016/S0040-4039(00)92333-5

upstream raw materials:

Met-OMe

N-tert-butoxycarbonyl-L-phenylalanine

(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride

s-methionine hydrochloride

Downstream raw materials:

boc-Tyr-Gly-Gly-Phe-Met-OH

methyl N-tert-butoxycarbonyl-L-tyrosyldiglycyl-L-phenylalanyl-L-methioninate

met-enkephalin

N-tert-Butyloxycarbonyl-glycyl-glycyl-L-phenylalanyl-L-methionin-methylester

Refernces

• 1、 Wang, Chao,Guo, Mengzhun,Qi, Rupeng,Shang, Qinyu,Liu, Qiang,Wang, Shan,Zhao, Long,Wang, Rui,Xu, Zhaoqing. "Visible-Light-Driven, Copper-Catalyzed Decarboxylative C(sp3)?H Alkylation of Glycine and Peptides". supporting information. p. 15841 - 15846. Retrieved 2018/11/23.
• 2、 Azzouz, Rabah,Petit, Sylvain,Rouchet, Jean-Baptiste,Bischoff, Laurent. "A one-pot saponification-coupling sequence suitable for C-terminus peptide elongation using lithium carboxylates". supporting information. p. 1843 - 1846. Retrieved 2014/08/18.