Methyl N-[(benzyloxy)carbonyl]glycylphenylalaninate

Base Information

• Chemical Name: Methyl N-[(benzyloxy)carbonyl]glycylphenylalaninate
• CAS No.: 6206-42-4
• Molecular Formula: C20H22 N2 O5
• Molecular Weight: 370.405
• NSC Number: 169165
• DSSTox Substance ID: DTXSID50305118
• Mol file: 6206-42-4.mol

Synonyms:6206-42-4;NSC169165;SCHEMBL330432;DTXSID50305118;NSC-169165;Methyl N-[(benzyloxy)carbonyl]glycylphenylalaninate

Chemical Property of Methyl N-[(benzyloxy)carbonyl]glycylphenylalaninate

Chemical Property:

• Vapor Pressure: 3.83E-14mmHg at 25°C
• Boiling Point: 595.4°Cat760mmHg
• Flash Point: 313.9°C
• Density: 1.218g/cm³
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 370.15287181
• Heavy Atom Count: 27
• Complexity: 485

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC=CC=C1)NC(=O)CNC(=O)OCC2=CC=CC=C2

Technology Process of Methyl N-[(benzyloxy)carbonyl]glycylphenylalaninate

There total 26 articles about Methyl N-[(benzyloxy)carbonyl]glycylphenylalaninate 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: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + Z-Gly-(L)-Phe (1170-76-9) → N-benzyloxycarbonylglycyl-L-phenylalanine methyl ester (6206-42-4)

Guidance literature:

In diethyl ether;

DOI:10.1039/b108738j

Reference yield: 98.0%

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + N-(Benzyloxycarbonyl)glycine (1138-80-3) → N-benzyloxycarbonylglycyl-L-phenylalanine methyl ester (6206-42-4)

Guidance literature:

In water; ethyl acetate; tert-butyl alcohol; for 10h; immobilized thermolysin;

DOI:10.1271/bbb1961.54.1433

Reference yield: 92.0%

methanol (67-56-1) + (S)-tert-butyl 2-(2-(((benzyloxy)carbonyl)amino)acetamido)-3-phenylpropanoate (101399-00-2,16881-36-0) → N-benzyloxycarbonylglycyl-L-phenylalanine methyl ester (6206-42-4)

Guidance literature:

With cross-linked enzyme aggregates of Alcalase; at 50 ℃; for 48h; Molecular sieve; Enzymatic reaction;

DOI:10.1002/adsc.201000313

upstream raw materials:

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

N-(Benzyloxycarbonyl)glycine

1-(N-benzyloxycarbonyl-glycyloxy)-piperidine

Z-glycine-OTCP

Downstream raw materials:

Z-Gly-(L)-Phe

N-(benzyloxycarbonyl)-glycyl-L-phenylalanyl-L-leucine amide

N-(Benzyloxycarbonyl)glycine

Cbz-glycylphenylalanyl hydrazide

Refernces

• 1、 Erapalapati, Venkataramana,Hale, Umatai A.,Madhavan, Nandita. "Phosphorus pentoxide for amide and peptide bond formation with minimal by-products". supporting information. . Retrieved 2019/11/21.
• 2、 Terrey, Myles J.,Perry, Carole C.,Cross, Warren B.. "Postsynthetic Modification of Phenylalanine Containing Peptides by C-H Functionalization". . p. 104 - 108. Retrieved 2019/01/11.