Z-Asn(trt)-OH

Base Information

• Chemical Name: Z-Asn(trt)-OH
• CAS No.: 132388-57-9
• Molecular Formula: C31H28N2O5
• Molecular Weight: 508.574
• DSSTox Substance ID: DTXSID70568889
• Nikkaji Number: J1.823.779B
• Wikidata: Q72516510
• Mol file: 132388-57-9.mol

Synonyms:Z-ASN(TRT)-OH;132388-57-9;N-Cbz-N'-trityl-L-asparagine;(S)-2-(((Benzyloxy)carbonyl)amino)-4-oxo-4-(tritylamino)butanoic acid;(2S)-4-oxo-2-(phenylmethoxycarbonylamino)-4-(tritylamino)butanoic acid;Z-L-Asn(Trt)-OH;Z-Ngamma-trityl-L-asparagine;MFCD00153326;C31H28N2O5;N2-CBZ-N4-trityl-L-asparagine;DTXSID70568889;FPVBKISSJULIGI-MHZLTWQESA-N;AKOS015892638;FD21144;CS-15745;CS-0042253;N-ALFA-Z-N-GAMMA-TRITYL-L-ASPARAGINE;N2-((Benzyloxy)carbonyl)-N4-trityl-L-asparagine;J-300054;N~2~-[(Benzyloxy)carbonyl]-N-(triphenylmethyl)-L-asparagine

Chemical Property of Z-Asn(trt)-OH

Chemical Property:

• Refractive Index: 1.619
• Boiling Point: 775.979 °C at 760 mmHg
• PKA: 3.88±0.10(Predicted)
• Flash Point: 423.097 °C
• PSA: 104.73000
• Density: 1.253 g/cm³
• LogP: 5.64620
• Storage Temp.: -15°C
• XLogP3: 5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 508.19982200
• Heavy Atom Count: 38
• Complexity: 717

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-2-(((Benzyloxy)carbonyl)amino)-4-oxo-4-(tritylamino)butanoic acid 95+% ^*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(CC(=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](CC(=O)NC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)C(=O)O

Technology Process of Z-Asn(trt)-OH

There total 3 articles about Z-Asn(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:

triphenylmethyl alcohol (76-84-6) + N-benzyloxycarbonyl-L-asparagine (2304-96-3) → N-benzyloxycarbonyl-N'-trityl-L-asparagine (132388-57-9)

Guidance literature:

With sulfuric acid; acetic anhydride; In acetic acid; at 50 ℃; for 1h;

DOI:10.1016/S0040-4039(00)74872-6

Reference yield:

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + (S)-2-Amino-N-trityl-succinamic acid (132388-58-0,200192-49-0) → N-benzyloxycarbonyl-N'-trityl-L-asparagine (132388-57-9)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/ol026799w

Reference yield:

triphenylmethyl alcohol (76-84-6) → N-benzyloxycarbonyl-N'-trityl-L-asparagine (132388-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂SO₄; AcOH; Ac₂O

2: Et₃N / dimethylformamide

With sulfuric acid; acetic anhydride; acetic acid; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/ol026799w

upstream raw materials:

triphenylmethyl alcohol

N-benzyloxycarbonyl-L-asparagine

N-(Benzyloxycarbonyloxy)succinimide

(S)-2-Amino-N-trityl-succinamic acid

Downstream raw materials:

(S)-2-Amino-N-trityl-succinamic acid

(S)-3-carbonylbenzyloxy-4-(triphenylmethylaminoacetoyl)-oxazolidin-5-one

Z-Asn(Trt)-Leu-Aib-Pro-Ser(t-Bu)-OMe

N²-benzyloxycarbonyl-N²-methyl-L-asparagine

Refernces

• 1、 Aurelio, Luigi,Brownlee, Robert T. C.,Hughes, Andrew B.. "A novel synthesis of N-methyl asparagine, arginine, histidine, and tryptophan". . p. 3767 - 3769. Retrieved 2007/10/03.
• 2、 Sieber,Riniker. "Protection of carboxamide functions by the trityl residue. Application to peptide synthesis". . p. 739 - 742. Retrieved 2007/10/02.