(S)-3-(((Allyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)propanoic acid

Base Information

• Chemical Name: (S)-3-(((Allyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)propanoic acid
• CAS No.: 161561-83-7
• Molecular Formula: C₁₂H₂₀N₂O₆
• Molecular Weight: 288.301
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID50420698
• Nikkaji Number: J1.388.215K
• Wikidata: Q72510470
• Mol file: 161561-83-7.mol

Synonyms:161561-83-7;(S)-3-(((Allyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)propanoic acid;BOC-DAP(ALOC)-OH;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(prop-2-enoxycarbonylamino)propanoic acid;Boc-Dap(Alloc)-OH;Boc-L-Dap(Aloc)-OH;SCHEMBL14265360;Boc-Dap(Alloc)-OH, AldrichCPR;DTXSID50420698;AUPOSBLDRPESJX-QMMMGPOBSA-N;Nalpha-Boc-Nbeta-allyloxycarbonyl-L-2,3-diaminopropionic acid;AMY22543;MFCD00798611;(S)-3-(((Allyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)propanoicacid;AKOS016843229;BS-21659;CS-0208903;EN300-7374605;A883089;N-(tert-Butoxycarbonyl)-3-(allyloxycarbonylamino)-L-alanine;(S)-3-(allyloxycarbonylamino)-2-(tert-butoxycarbonylamino)propanoic acid;N-(tert-Butoxycarbonyl)-3-({[(prop-2-en-1-yl)oxy]carbonyl}amino)-L-alanine;N-[(1,1-Dimethylethoxy)carbonyl]-3-[[(2-propen-1-yloxy)carbonyl]amino]-L-alanine;N-alpha-t-Butyloxycarbonyl-N-beta-allyloxycarbonyl-L-2,3-diaminopropionic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-{[(prop-2-en-1-yloxy)carbonyl]amino}propanoic acid;N-alpha-t-Butyloxycarbonyl-N-beta-allyloxycarbonyl-L-2,3-diaminopropionic acid (Boc-L-Dap(Alloc)-OH)

Chemical Property of (S)-3-(((Allyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)propanoic acid

Chemical Property:

• Boiling Point: 470.5±45.0 °C(Predicted)
• PKA: 3.67±0.10(Predicted)
• PSA: 113.96000
• Density: 1.194
• LogP: 1.65830
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 288.13213636
• Heavy Atom Count: 20
• Complexity: 375

Purity/Quality:

97% ^*data from raw suppliers

N-alpha-Boc-Nbeta-allyloxycarbonyl-L-2,3-diaminopropionic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CNC(=O)OCC=C)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CNC(=O)OCC=C)C(=O)O

Technology Process of (S)-3-(((Allyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)propanoic acid

There total 2 articles about (S)-3-(((Allyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)propanoic 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: 85.0%

(R)-2-tert-butoxycarbonyl-3-aminopropionic acid (73259-81-1,113625-76-6,76387-70-7) + Allyl chloroformate (2937-50-0) → (R)-3-(((allyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)propanoic acid (161561-83-7,179251-60-6)

Guidance literature:

With potassium carbonate; In 1,4-dioxane; water; at 20 ℃; for 16h;

DOI:10.1021/acs.jmedchem.1c01975

Reference yield:

(S)-3-amino-2-tert-butoxycarbonylaminopropionic acid (76387-70-7) + Allyl chloroformate (2937-50-0) → Boc-Dap(Alloc)-OH (161561-83-7,179251-60-6)

Guidance literature:

With potassium hydrogencarbonate; In tetrahydrofuran; at 20 ℃; for 1h; Cooling with ice;

DOI:10.1021/jacs.8b13157 DOI:10.1021/jacs.8b13157

Reference yield:

(R)-3-(((allyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)propanoic acid (161561-83-7,179251-60-6) → C21H32N4O6S

Guidance literature:

Multi-step reaction with 3 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile / 1 h / 20 °C / Inert atmosphere

2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / methanol / 2 h / 20 °C / Inert atmosphere

3: lithium hydroxide / methanol; water / 16 h / 40 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hydroxide; In methanol; water; acetonitrile;

DOI:10.1021/acs.jmedchem.1c01975

upstream raw materials:

(S)-3-amino-2-tert-butoxycarbonylaminopropionic acid

Allyl chloroformate

(R)-2-tert-butoxycarbonyl-3-aminopropionic acid

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