2-[[2,4-Dicarboxybutyl(hydroxy)phosphoryl]methyl]pentanedioic acid

Base Information

• Chemical Name: 2-[[2,4-Dicarboxybutyl(hydroxy)phosphoryl]methyl]pentanedioic acid
• CAS No.: 229472-51-9
• Molecular Formula: C₁₂H₁₉O₁₀P
• Molecular Weight: 354.251
• European Community (EC) Number: 630-753-6
• DSSTox Substance ID: DTXSID70274433
• Nikkaji Number: J1.816.625I
• ChEMBL ID: CHEMBL134749
• Mol file: 229472-51-9.mol

Synonyms:PBDA;229472-51-9;FN-6;CHEMBL134749;2-[[2,4-dicarboxybutyl(hydroxy)phosphoryl]methyl]pentanedioic acid;SCHEMBL4135913;2-[(2,4-Dicarboxy-butyl)-hydroxy-phosphinoylmethyl]-pentanedioic acid;DTXSID70274433;PBDA, >95% (NMR), liquid;BDBM50085699;4,4'-Phosphonicobis(butane-1,3-dicarboxylic acid);J-014911;4-Carboxy-5-[(2,4-dicarboxy-butyl)-hydroxy-phosphinoyl]-pentanoic acid;(meso)4-Carboxy-5-[(2,4-dicarboxy-butyl)-hydroxy-phosphinoyl]-pentanoic acid;(S,S / R,R)4-Carboxy-5-[(2,4-dicarboxy-butyl)-hydroxy-phosphinoyl]-pentanoic acid

Chemical Property of 2-[[2,4-Dicarboxybutyl(hydroxy)phosphoryl]methyl]pentanedioic acid

Chemical Property:

• PSA: 196.31000
• LogP: 0.38800
• Storage Temp.: −20°C
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 354.07158380
• Heavy Atom Count: 23
• Complexity: 472

Purity/Quality:

97% ^*data from raw suppliers

PBDA 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CC(=O)O)C(CP(=O)(CC(CCC(=O)O)C(=O)O)O)C(=O)O

Technology Process of 2-[[2,4-Dicarboxybutyl(hydroxy)phosphoryl]methyl]pentanedioic acid

There total 9 articles about 2-[[2,4-Dicarboxybutyl(hydroxy)phosphoryl]methyl]pentanedioic 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: 89.0%

4-tert-Butoxycarbonyl-5-[tert-butoxy-(2,4-dicarboxy-butyl)-phosphinoyl]-pentanoic acid tert-butyl ester (229472-48-4) → 4,4'-phosphinicobis(butane-1,3-dicarboxylic acid) (229472-51-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jm0001774

Reference yield:

5-[Benzyloxy-(2,4-bis-benzyloxycarbonyl-butyl)-phosphinoyl]-4-benzyloxycarbonyl-pentanoic acid benzyl ester (263393-92-6) → 4,4'-phosphinicobis(butane-1,3-dicarboxylic acid) (229472-51-9)

Guidance literature:

With hydrogen; palladium dihydroxide; at 20 ℃; for 24h; under 3620.04 Torr;

DOI:10.1021/jm9905559

Reference yield:

dibenzyl 2-methylenepentanedioate (173039-05-9) → 4,4'-phosphinicobis(butane-1,3-dicarboxylic acid) (229472-51-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH / tetrahydrofuran / 3 h / 20 °C

2: H₂ / 10percentPd/C / ethyl acetate / 16 h / 20 °C / 3102.97 Torr

3: 89 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

With hydrogen; sodium hydride; trifluoroacetic acid; 10percentPd/C; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jm0001774

upstream raw materials:

5-[Benzyloxy-(2,4-bis-benzyloxycarbonyl-butyl)-phosphinoyl]-4-benzyloxycarbonyl-pentanoic acid benzyl ester

4-tert-Butoxycarbonyl-5-[tert-butoxy-(2,4-dicarboxy-butyl)-phosphinoyl]-pentanoic acid tert-butyl ester

2-methylenepentanedioic acid di-tert-butyl ester

dibenzyl 2-methylenepentanedioate