(S,S,S)-avenic acid A

Base Information

• Chemical Name: (S,S,S)-avenic acid A
• CAS No.: 76224-57-2
• Molecular Formula: C₁₂H₂₂N₂O₈
• Molecular Weight: 322.315
• DSSTox Substance ID: DTXSID201136365
• Metabolomics Workbench ID: 55790
• Wikidata: Q27117398
• Mol file: 76224-57-2.mol

Synonyms:(S,S,S)-avenic acid A;N-[(3S)-3-carboxy-3-{[(3S)-3-carboxy-3-hydroxypropyl]amino}propyl]-L-homoserine;N-[(3S)-3-Carboxy-3-[[(3S)-3-carboxy-3-hydroxypropyl]amino]propyl]-L-homoserine;SCHEMBL19473245;CHEBI:38154;DTXSID201136365;Q27117398;(2S)-4-[[(1S)-1-carboxy-3-hydroxypropyl]amino]-2-[[(3S)-3-carboxy-3-hydroxypropyl]amino]butanoic acid

Chemical Property of (S,S,S)-avenic acid A

Chemical Property:

• PSA: 176.42000
• LogP: -1.53810
• XLogP3: -6.6
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 13
• Exact Mass: 322.13761566
• Heavy Atom Count: 22
• Complexity: 376

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CNC(CCO)C(=O)O)C(C(=O)O)NCCC(C(=O)O)O
• Isomeric SMILES: C(CN[C@@H](CCO)C(=O)O)[C@@H](C(=O)O)NCC[C@@H](C(=O)O)O

Technology Process of (S,S,S)-avenic acid A

There total 7 articles about (S,S,S)-avenic acid A 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: 49.0%

(S)-4-(((S)-1-carboxy-3-(((S)-2-oxotetrahydrofuran-3-yl)amino)propyl)amino)-2-hydroxybutanoic acid → avenic acid A (76224-57-2)

Guidance literature:

With potassium hydroxide; In water; at 20 ℃; for 16h;

DOI:10.1002/chem.202004004

Reference yield:

(S)-2-{[(S)-3-Benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-tert-butoxycarbonyl-amino}-4-((S)-2-oxo-tetrahydro-furan-3-ylamino)-butyric acid benzyl ester (79438-09-8) → avenic acid A (76224-57-2)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen / 5 percent Pd/C / ethanol; H₂O / 0.5 h / Ambient temperature

2: 1.) 2.5 percent KOH, 2.) Dowex 50Wx₄ resin (H(+) form) / 1.) 14 h, room temperature

With potassium hydroxide; Dowex 50Wx₄ resin (H(+) form); hydrogen; palladium on activated charcoal; In ethanol; water;

DOI:10.1246/cl.1981.827

Reference yield:

L-tert-butoxycarbonyl-N<3-O-tetrahydropyranyl-3-carboxybenzylpropyl>homoserine aldehyde benzyl ester (77856-44-1,77881-92-6,79466-01-6,120964-21-8) → avenic acid A (76224-57-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / NaBH₃CN / methanol / 14 h / Ambient temperature

2: hydrogen / 5 percent Pd/C / ethanol; H₂O / 0.5 h / Ambient temperature

3: 1.) 2.5 percent KOH, 2.) Dowex 50Wx₄ resin (H(+) form) / 1.) 14 h, room temperature

With potassium hydroxide; Dowex 50Wx₄ resin (H(+) form); hydrogen; sodium cyanoborohydride; palladium on activated charcoal; In methanol; ethanol; water;

DOI:10.1246/cl.1981.827

upstream raw materials:

(S)-2-((S)-3-Acetoxy-3-ethoxycarbonyl-propylamino)-4-((S)-2-oxo-tetrahydro-furan-3-ylamino)-butyric acid tert-butyl ester

(S)-2-((S)-3-Carboxy-3-hydroxy-propylamino)-4-((S)-2-oxo-tetrahydro-furan-3-ylamino)-butyric acid; compound with trifluoro-acetic acid

(S)-2-Benzyloxycarbonylamino-4-((S)-2-oxo-tetrahydro-furan-3-ylamino)-butyric acid tert-butyl ester

(S)-2-{[(S)-3-Benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-tert-butoxycarbonyl-amino}-4-((S)-2-oxo-tetrahydro-furan-3-ylamino)-butyric acid benzyl ester

Downstream raw materials:

DL-Homoserine

malic acid

aspartic Acid