(S)-2,4-Bis(((benzyloxy)carbonyl)amino)butanoic acid

Base Information

• Chemical Name: (S)-2,4-Bis(((benzyloxy)carbonyl)amino)butanoic acid
• CAS No.: 55478-23-4
• Molecular Formula: C20H22 N2 O6
• Molecular Weight: 386.404
• DSSTox Substance ID: DTXSID60428605
• Nikkaji Number: J3.224.992B
• Wikidata: Q82241425
• Mol file: 55478-23-4.mol

Synonyms:55478-23-4;Z-DAB(Z)-OH;(S)-2,4-Bis(((benzyloxy)carbonyl)amino)butanoic acid;(2S)-2,4-bis(phenylmethoxycarbonylamino)butanoic Acid;Nalpha,gamma-Bis-Z-L-2,4-diaminobutyric acid;Na,g-Bis-Z-L-2,4-diaminobutyric acid;SCHEMBL18063383;DTXSID60428605;MFCD00236965;AKOS027340170;CS-16530;(S)-2,4-Bis(carbobenzoxyamino)butyric acid;CS-0099803;D76027;N-alpha,gamma-Bis-Z-L-2,4-diaminobutyric acid;(S)-2,4-bis(benzyloxycarbonylamino)butanoic acid;(S)-2,4-Bis(((benzyloxy)carbonyl)amino)butanoicacid;(2S)-2,4-Bis{[(benzyloxy)carbonyl]amino}butanoic acid;Butanoic acid,2,4-bis[[(phenylmethoxy)carbonyl]amino]-,(S)-(9ci)

Chemical Property of (S)-2,4-Bis(((benzyloxy)carbonyl)amino)butanoic acid

Chemical Property:

• Boiling Point: 646.1±55.0 °C(Predicted)
• PKA: 3.88±0.10(Predicted)
• PSA: 120.94000
• Density: 1.281±0.06 g/cm3(Predicted)
• LogP: 3.09130
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 386.14778643
• Heavy Atom Count: 28
• Complexity: 501

Purity/Quality:

98%Min ^*data from raw suppliers

N-alpha,γ-Bis-Z-L-2,4-diaminobutyric acid ^*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)NCCC(C(=O)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)NCC[C@@H](C(=O)O)NC(=O)OCC2=CC=CC=C2

Technology Process of (S)-2,4-Bis(((benzyloxy)carbonyl)amino)butanoic acid

There total 4 articles about (S)-2,4-Bis(((benzyloxy)carbonyl)amino)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: 79.0%

benzyl chloroformate (501-53-1,94274-21-2) + L-2,4-diaminobutyric acid monohydrochloride (1482-98-0) → (S)-2,4-bis(((benzyloxy)carbonyl)amino)butanoic acid (55478-23-4)

Guidance literature:

With sodium hydroxide; at 0 ℃;

DOI:10.1016/S0040-4039(00)60152-1

Reference yield: 64.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + (S)-2,4-diaminobutyric acid dihydrochloride (1482-98-0,1883-09-6,6970-28-1,19391-83-4,26889-08-7,40149-78-8,57538-26-8,65427-54-5,66837-03-4,89700-93-6,101854-78-8,127531-11-7) → (S)-2,4-bis(((benzyloxy)carbonyl)amino)butanoic acid (55478-23-4)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; water; for 15h;

Reference yield:

→ (S)-2-Amino-4-benzyloxycarbonylamino-butyric acid (2130-77-0) + (S)-2,4-bis(((benzyloxy)carbonyl)amino)butanoic acid (55478-23-4)

Guidance literature:

With sodium hydroxide; benzyl chloroformate;

upstream raw materials:

benzyl chloroformate

L-2,4-diaminobutyric acid monohydrochloride

N-(Benzyloxycarbonyloxy)succinimide

(S)-2,4-diaminobutyric acid dihydrochloride

Downstream raw materials:

6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(2,4-di(benzyloxycarbonylamino)-L-butyryl)sulfamoyl]adenosine

N-((S)-2,4-bis-benzyloxycarbonylamino-butyryl)-L-leucine

(3S)-3-benzyloxycarbonylamino-2-pyrrolidinone

N^α,N^γ-Di-Z-L-α,γ-Dab-N^γ-Z-L-α,γ-Dab-OMe

Refernces

• 1、 Jones,Crockett, Alan K.. "The synthesis of unusual tetrahydropyrimidine amino acids". . p. 7459 - 7462. Retrieved 2007/10/02.