(R)-2-Amino-4-oxo-4-(tritylamino)butanoic acid

Base Information

• Chemical Name: (R)-2-Amino-4-oxo-4-(tritylamino)butanoic acid
• CAS No.: 200192-49-0
• Molecular Formula: C₂₃H₂₂N₂O₃
• Molecular Weight: 374.439
• Hs Code.: 2924199090
• Mol file: 200192-49-0.mol

Synonyms:(R)-2-Amino-4-oxo-4-(tritylamino)butanoic acid;N4-Trityl-D-asparagine;SCHEMBL21690461;MFCD00236802;AKOS030213026;CS-17347;CS-0166742;N-beta-Trityl-D-asparagine (Trt-D-Asn-OH);(R)-2-Amino-4-oxo-4-(tritylamino)butanoicacid

Chemical Property of (R)-2-Amino-4-oxo-4-(tritylamino)butanoic acid

Chemical Property:

• Boiling Point: 641.208ºC at 760 mmHg
• Flash Point: 341.59ºC
• PSA: 101.65000
• Density: 1.234 g/cm3
• LogP: 3.92360
• Storage Temp.: Store at 0°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 374.16304257
• Heavy Atom Count: 28
• Complexity: 472

Purity/Quality:

99% ^*data from raw suppliers

H-D-Asn(Trt)-OH 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (R)-2-Amino-4-oxo-4-(tritylamino)butanoic acid

There total 4 articles about (R)-2-Amino-4-oxo-4-(tritylamino)butanoic acid 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: 95.0%

L-Asn(Trt) (132388-59-1) → (S)-2-Amino-N-trityl-succinamic acid (132388-58-0,200192-49-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 50 ℃; for 12h;

DOI:10.1007/s00726-013-1625-7

Reference yield: 77.0%

triphenylmethyl alcohol (76-84-6) + L-asparagine (70-47-3,28088-48-4,7006-34-0) → (S)-2-Amino-N-trityl-succinamic acid (132388-58-0,200192-49-0)

Guidance literature:

With sulfuric acid; acetic anhydride; acetic acid; at 60 ℃; for 3h;

DOI:10.1002/chem.202000117

Reference yield:

N-benzyloxycarbonyl-N'-trityl-L-asparagine (132388-57-9) → (S)-2-Amino-N-trityl-succinamic acid (132388-58-0,200192-49-0)

Guidance literature:

With hydrogen; palladium on activated charcoal;

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

upstream raw materials:

triphenylmethyl alcohol

L-asparagine

N-benzyloxycarbonyl-N'-trityl-L-asparagine

L-Asn(Trt)

Downstream raw materials:

tert-butyl 4-((S)-3-(((S)-1-(tert-butyloxy)-1-oxopropan-2-yl)amino)-2-(2-((5S,8S)-6-(tertbutoxycarbonyl)-8-carbamoyl-12,12-dimethyl-3,10-dioxo-1,1,1-triphenyl-11-oxa-2,6,9-triazatridecan-5-yl)-6-((tert-butyloxycarbonyl)amino)pyrimidine-4-carboxamido)-3-oxopropyl)-1H-imidazole-1-carboxylate

2-((5S,8S)-6-(tert-butyloxycarbonyl)-8-carbamoyl-12,12-dimethyl-3,10-dioxo-1,1,1-triphenyl-11-oxa-2,6,9-triazatridecan-5-yl)-6-((tert-butyloxycarbonyl)amino)pyrimidine-4-carboxylic acid

tert-butyl 2-((5S,8S)-6-(tert-butyloxycarbonyl)-8-carbamoyl-12,12-dimethyl-3,10-dioxo-1,1,1-triphenyl-11-oxa-2,6,9-triazatridecan-5-yl)-6-((tert-butyloxycarbonyl)amino)-pyrimidine-4-carboxylate

(S)-3-((tert-butyloxycarbonyl)((S)-1-(4-(tert-butyloxycarbonyl)-6-((tert-butyloxycarbonyl)-amino)pyrimidin-2-yl)-3-oxo-3-(tritylamino)propyl)amino)-2-((tert-butyloxycarbonyl)-amino)propanoic acid

Refernces

• 1、 Chen, Chun-Chi,Rajagopal, Basker,Liu, Xuan Yu,Chen, Kuan Lin,Tyan, Yu-Chang,Lin, Fui,Lin, Po-Chiao. "A mild removal of Fmoc group using sodium azide". . p. 367 - 374. Retrieved 2014/03/21.
• 2、 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.