tert-butyloxycarbonyl-glycylphenylalanine

Base Information

• Chemical Name: tert-butyloxycarbonyl-glycylphenylalanine
• CAS No.: 4530-37-4
• Molecular Formula: C16H22 N2 O5
• Molecular Weight: 322.361
• Mol file: 4530-37-4.mol

Synonyms:Alanine,N-(N-carboxyglycyl)-3-phenyl-, N-tert-butyl ester, L- (8CI); L-Phenylalanine,N-[N-[(1,1-dimethylethoxy)carbonyl]glycyl]-;N-(tert-Butoxycarbonyl)glycylphenylalanine;N-(tert-Butyloxycarbonyl)glycyl-L-phenylalanine

Chemical Property of tert-butyloxycarbonyl-glycylphenylalanine

Chemical Property:

• Vapor Pressure: 1.27E-13mmHg at 25°C
• Boiling Point: 565.4°Cat760mmHg
• Flash Point: 295.8°C
• PSA: 104.73000
• Density: 1.204g/cm³
• LogP: 2.10500

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyloxycarbonyl-glycylphenylalanine

There total 20 articles about tert-butyloxycarbonyl-glycylphenylalanine 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: 94.0%

di-tert-butyl dicarbonate (24424-99-5) + Gly-Phe-OH (3321-03-7) → N-t-butyloxycarbonylglycyl-L-phenylalanine (4530-37-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 25 ℃; for 2.25h;

DOI:10.1021/jm00354a006

Reference yield: 90.0%

methyl (2S)-2-[[2-(t-butoxycarbonylamino)acetyl]amino]-3-phenylpropanoate (106624-70-8,41889-06-9) → N-t-butyloxycarbonylglycyl-L-phenylalanine (4530-37-4)

Guidance literature:

With chlorotriisopropylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1007/s10989-018-9680-2

Reference yield: 88.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + Boc-Gly-OPCP (17693-18-4) → N-t-butyloxycarbonylglycyl-L-phenylalanine (4530-37-4)

Guidance literature:

With sodium hydroxide; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at -5 ℃;

DOI:10.1016/S0223-5234(98)80060-3

upstream raw materials:

BOC-glycine

(L)-phenylalanine ethyl ester hydrochloride

di-tert-butyl dicarbonate

Gly-Phe-OH

Downstream raw materials:

Boc-Gly-Phe-OSu

(Boc-Gly-L-Phe-L-Cys-Gly-OCH₃)2

Boc-Gly-L-Phe-L-Cys-Gly-OCH₃

Boc-Gly-L-Phe-L-Cys(S-Cbz-L-Ala)-Gly-OCH₃

Refernces

• 1、 Uspenskaya, Anastasiya A.,Machulkin, Alexey E.,Nimenko, Ekaterina A.,Shafikov, Radik R.,Petrov, Stanislav A.,Skvortsov, Dmitry A.,Beloglazkina, Elena K.,Majouga, Alexander G.. "Influence of the dipeptide linker configuration on the activity of PSMA ligands". . p. 756 - 759. Retrieved 2021/01/12.
• 2、 Sayes, Morgane,Charette, André B.. "Diphenylsilane as a coupling reagent for amide bond formation". supporting information. p. 5060 - 5064. Retrieved 2017/11/09.