N-(Triphenylmethyl)-L-threonine

Base Information

• Chemical Name: N-(Triphenylmethyl)-L-threonine
• CAS No.: 80514-76-7
• Molecular Formula: C23H23NO3
• Molecular Weight: 361.441
• DSSTox Substance ID: DTXSID00557160
• Nikkaji Number: J743.272K
• Mol file: 80514-76-7.mol

Synonyms:N-(Triphenylmethyl)-L-threonine;SCHEMBL6746239;DTXSID00557160;AKOS030214475;CS-0209020;(2S,3R)-3-hydroxy-2-(tritylamino)butanoic acid

Chemical Property of N-(Triphenylmethyl)-L-threonine

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 361.16779360
• Heavy Atom Count: 27
• Complexity: 417

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of N-(Triphenylmethyl)-L-threonine

There total 2 articles about N-(Triphenylmethyl)-L-threonine 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: 59.0%

L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + trityl chloride (76-83-5) → N-triphenylmethyl-(L)-threonine (80514-76-7)

Guidance literature:

L-threonine; With chloro-trimethyl-silane; In dichloromethane; for 0.333333h; Inert atmosphere; Reflux;

With triethylamine; In dichloromethane; at 0 ℃; for 0.916667h; Inert atmosphere;

trityl chloride; With triethylamine; In methanol; dichloromethane; at 0 - 20 ℃; for 20h; Inert atmosphere;

DOI:10.1016/j.tet.2014.06.011

Reference yield:

trityl chloride (76-83-5) + (5S,6R)-5-Amino-6-methyl-2,2-diphenyl-[1,3,2]dioxasilinan-4-one → N-triphenylmethyl-(L)-threonine (80514-76-7)

Guidance literature:

With methanol; triethylamine; Multistep reaction; 1.) CH₂Cl₂, room temp., 5 h;

DOI:10.1021/jo00346a031

Reference yield: 92.0%

N-triphenylmethyl-(L)-threonine (80514-76-7) → (3S,4R)-4-Methyl-3-(trityl-amino)-oxetan-2-one

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In dichloromethane;

DOI:10.1016/0040-4039(96)00805-2

upstream raw materials:

trityl chloride

L-threonine

Downstream raw materials:

N-trityl-L-threonine benzyl ester

Trt-Thr-NHBn

Trt-(3-Me-Azy)-NHBn

Trt-(3-Me-Azy)-Ala-NHMe