1,4-Dimethyl N-(triphenylmethyl)-L-aspartate

Base Information

• Chemical Name: 1,4-Dimethyl N-(triphenylmethyl)-L-aspartate
• CAS No.: 116393-72-7
• Molecular Formula: C25H25NO4
• Molecular Weight: 403.478
• DSSTox Substance ID: DTXSID101259881
• Nikkaji Number: J3.140.198D
• Mol file: 116393-72-7.mol

Synonyms:SCHEMBL5799829;DTXSID101259881;116393-72-7;1,4-Dimethyl N-(triphenylmethyl)-L-aspartate

Chemical Property of 1,4-Dimethyl N-(triphenylmethyl)-L-aspartate

Chemical Property:

• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 403.17835828
• Heavy Atom Count: 30
• Complexity: 500

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of 1,4-Dimethyl N-(triphenylmethyl)-L-aspartate

There total 4 articles about 1,4-Dimethyl N-(triphenylmethyl)-L-aspartate 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%

dimethyl L-aspartate hydrochloride (32213-95-9) + trityl chloride (76-83-5) → dimethyl (2S)-N-(triphenylmethyl)aspartate (116393-72-7)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/b912782h

Reference yield: 100.0%

L-Aspartic acid dimethyl ester (6384-18-5) + trityl chloride (76-83-5) → dimethyl (2S)-N-(triphenylmethyl)aspartate (116393-72-7)

Guidance literature:

With triethylamine; In dichloromethane; Inert atmosphere;

DOI:10.1021/jo3022583

Reference yield: 95.0%

DL-aspartic acid dimethyl ester hydrochloride (32213-95-9) + trityl chloride (76-83-5) → dimethyl (2S)-N-(triphenylmethyl)aspartate (116393-72-7)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 3h;

upstream raw materials:

DL-aspartic acid dimethyl ester hydrochloride

trityl chloride

dimethyl L-aspartate hydrochloride

L-Aspartic acid dimethyl ester

Downstream raw materials:

dimethyl (2S,3S)-N-tritylamino-β-3-fluorobenzyl aspartate

dimethyl (2S,3R)-N-tritylamino-β-3-fluorobenzyl aspartate

Refernces

• 1、 Bell, Jonathan D.,Harkiss, Alexander H.,Nobis, David,Malcolm, Eilidh,Knuhtsen, Astrid,Wellaway, Christopher R.,Jamieson, Andrew G.,Magennis, Steven W.,Sutherland, Andrew. "Conformationally rigid pyrazoloquinazoline α-amino acids: One- And two-photon induced fluorescence". supporting information. p. 1887 - 1890. Retrieved 2020/02/22.
• 2、 Gilfillan, Lynne,Artschwager, Raik,Harkiss, Alexander H.,Liskamp, Rob M. J.,Sutherland, Andrew. "Synthesis of pyrazole containing α-amino acids via a highly regioselective condensation/aza-Michael reaction of β-aryl α,β-unsaturated ketones". supporting information. p. 4514 - 4523. Retrieved 2015/04/14.