Z-Gln(Trt)-OH

Base Information

• Chemical Name: Z-Gln(Trt)-OH
• CAS No.: 132388-60-4
• Molecular Formula: C32H30N2O5
• Molecular Weight: 522.601
• DSSTox Substance ID: DTXSID00449899
• Wikidata: Q72516515
• Mol file: 132388-60-4.mol

Synonyms:Z-Gln(Trt)-OH;132388-60-4;Cbz-Gln(Trt)-OH;(2S)-5-oxo-2-(phenylmethoxycarbonylamino)-5-(tritylamino)pentanoic acid;n-cbz-n'-trityl-l-glutamine;MFCD00144845;(S)-2-(((Benzyloxy)carbonyl)amino)-5-oxo-5-(tritylamino)pentanoic acid;Z-Ndelta-trityl-L-glutamine;SCHEMBL18052437;DTXSID00449899;MYOAIKMOWHPBQS-NDEPHWFRSA-N;AKOS015960791;FD21525;AC-12304;AS-19306;CS-0146444;N2-((Benzyloxy)carbonyl)-N5-trityl-L-glutamine;J-300130;(S)-2-(benzyloxycarbonylamino)-5-oxo-5-(tritylamino)pentanoic acid

Chemical Property of Z-Gln(Trt)-OH

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 160-1650oC
• Refractive Index: 1.613
• Boiling Point: 792.6 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 433.2 °C
• PSA: 104.73000
• Density: 1.237 g/cm³
• LogP: 6.03630
• Storage Temp.: -15°C
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 522.21547206
• Heavy Atom Count: 39
• Complexity: 732

Purity/Quality:

99% ^*data from raw suppliers

Z-Gln(trt)-oh ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CCC(=O)NC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CCC(=O)NC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)C(=O)O

Technology Process of Z-Gln(Trt)-OH

There total 4 articles about Z-Gln(Trt)-OH 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: 77.0%

→ (S)-2-(((benzyloxy)carbonyl)amino)-5-oxo-5-(tritylamino)pentanoic acid (132388-60-4,200625-96-3)

Guidance literature:

Reference yield: 73.0%

triphenylmethyl alcohol (76-84-6) + Cbz-L-Gln (2650-64-8) → (S)-2-(((benzyloxy)carbonyl)amino)-5-oxo-5-(tritylamino)pentanoic acid (132388-60-4,200625-96-3)

Guidance literature:

With acetic anhydride; acetic acid; at 50 ℃; for 2h;

DOI:10.1021/ja402875h

Reference yield:

L-glutamine (56-85-9,26700-71-0) → (S)-2-(((benzyloxy)carbonyl)amino)-5-oxo-5-(tritylamino)pentanoic acid (132388-60-4,200625-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / toluene; water / 20 °C

2: sulfuric acid; acetic anhydride / 2 h / 50 °C

With sulfuric acid; acetic anhydride; sodium hydrogencarbonate; In water; toluene;

DOI:10.1080/00397911.2017.1315671

upstream raw materials:

triphenylmethyl alcohol

Cbz-L-Gln

L-glutamine

benzyl chloroformate

Downstream raw materials:

(S)-tert-butyl 2-amino-5-oxo-5-(tritylamino)pentanoate

benzyl (S)-(1-(methoxy(methyl)amino)-1,5-dioxo-5-(tritylamino)pentan-2-yl)carbamate

C₄₇H₅₁N₃O₇

Refernces

• 1、 Eildal, Jonas N. N.,Hultqvist, Greta,Balle, Thomas,Stuhr-Hansen, Nicolai,Padrah, Shahrokh,Gianni, Stefano,Stromgaard, Kristian,Jemth, Per. "Probing the role of backbone hydrogen bonds in protein-peptide interactions by amide-to-ester mutations". supporting information. p. 12998 - 13007. Retrieved 2013/09/24.
• 2、 Stefania, Rachele,Tei, Lorenzo,Barge, Alessandro,Crich, Simonetta Geninatti,Szabo, Ibolya,Cabella, Claudia,Cravotto, Giancarlo,Aime, Silvio. "Tuning glutamine binding modes in Gd-DOTA-based probes for an improved MRI visualization of tumor cells". experimental part. p. 76 - 85. Retrieved 2009/07/17.