(2R)-3-(Benzyloxycarbonylamino)-2-benzylpropanoic acid

Base Information

• Chemical Name: (2R)-3-(Benzyloxycarbonylamino)-2-benzylpropanoic acid
• CAS No.: 132696-47-0
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.353
• DSSTox Substance ID: DTXSID001160833
• Nikkaji Number: J2.136.302B
• Mol file: 132696-47-0.mol

Synonyms:132696-47-0;SCHEMBL7077000;DTXSID001160833;EN300-19448733;(2R)-3-(Benzyloxycarbonylamino)-2-benzylpropanoic acid;(2R)-2-benzyl-3-{[(benzyloxy)carbonyl]amino}propanoic acid;(alphaR)-alpha-[[[(Phenylmethoxy)carbonyl]amino]methyl]benzenepropanoic acid

Chemical Property of (2R)-3-(Benzyloxycarbonylamino)-2-benzylpropanoic acid

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 313.13140809
• Heavy Atom Count: 23
• Complexity: 373

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(CNC(=O)OCC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)C[C@H](CNC(=O)OCC2=CC=CC=C2)C(=O)O

Technology Process of (2R)-3-(Benzyloxycarbonylamino)-2-benzylpropanoic acid

There total 20 articles about (2R)-3-(Benzyloxycarbonylamino)-2-benzylpropanoic 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: 67.0%

[(R)-2-Benzyl-3-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-3-oxo-propyl]-carbamic acid benzyl ester (202932-29-4) → (R)-2-(benzyloxycarbonylaminomethyl)-3-phenylpropanoic acid (132696-47-0)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃;

DOI:10.1039/a706163c

Reference yield: 64.0%

benzyl (R)-2-benzyl-3-oxo-3-[(3aS,7aS)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]propylcarbamate (1605314-25-7) → (R)-2-(benzyloxycarbonylaminomethyl)-3-phenylpropanoic acid (132696-47-0)

Guidance literature:

With lithium hydroxide monohydrate; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 0.5h;

DOI:10.1002/ejoc.201301834

Reference yield:

benzyl (R)-2-benzyl-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-3-oxopropylcarbamate (1391826-39-3) → (R)-2-(benzyloxycarbonylaminomethyl)-3-phenylpropanoic acid (132696-47-0)

Guidance literature:

With lithium hydroxide monohydrate; dihydrogen peroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 3h;

DOI:10.1002/chem.201200313

upstream raw materials:

[(R)-2-Benzyl-3-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-3-oxo-propyl]-carbamic acid benzyl ester

benzyloxycarbonylaminomethyl acetate

(4S,5R)-4-Methyl-5-phenyl-3-(3-phenyl-propionyl)-oxazolidin-2-one

(R)-3-Benzyl-4-((4S,5R)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-4-oxo-butyric acid

Downstream raw materials:

(R)-α-benzyl-β-aminopropanoic acid

benzyl (R)-2-benzyl-3-(2-fluoroethylamino)-3-oxopropylcarbamate