Butanedioic acid, 2,3-dihydroxy-2-((4-hydroxyphenyl)methyl)-, (2R,3S)-

Base Information

• Chemical Name: Butanedioic acid, 2,3-dihydroxy-2-((4-hydroxyphenyl)methyl)-, (2R,3S)-
• CAS No.: 35388-57-9
• Molecular Formula: C₁₁H₁₂O₇
• Molecular Weight: 256.212
• UNII: 511BQ884F7
• Mol file: 35388-57-9.mol

Synonyms:(p-hydroxybenzyl)tartaric acid;piscidic acid;piscidic acid, (S-(R*,S*))-isomer

Chemical Property of Butanedioic acid, 2,3-dihydroxy-2-((4-hydroxyphenyl)methyl)-, (2R,3S)-

Chemical Property:

• Vapor Pressure: 1.3E-11mmHg at 25°C
• Boiling Point: 519.4°C at 760 mmHg
• Flash Point: 282°C
• Density: 1.654g/cm³
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 256.05830272
• Heavy Atom Count: 18
• Complexity: 321

Purity/Quality:

90%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(C(=O)O)O)(C(=O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1C[C@@]([C@@H](C(=O)O)O)(C(=O)O)O)O

Technology Process of Butanedioic acid, 2,3-dihydroxy-2-((4-hydroxyphenyl)methyl)-, (2R,3S)-

There total 11 articles about Butanedioic acid, 2,3-dihydroxy-2-((4-hydroxyphenyl)methyl)-, (2R,3S)- 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: 95.0%

dimethyl (2R,3S)-2,3-dihydroxy-2-(4-hydroxybenzyl)succinate (51705-36-3) → (2S,3R)-(+)-piscidic acid (35388-57-9)

Guidance literature:

With potassium hydroxide; In methanol; for 1h; Heating;

DOI:10.1271/bbb.63.964

Reference yield:

4-hydroxyphenylpiruvic acid (156-39-8) → (2S,3R)-(+)-piscidic acid (35388-57-9)

Guidance literature:

Multi-step reaction with 6 steps

1: diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

2: benzene / 2 h / Heating

3: 99 percent / imidazole / dimethylformamide / 5 h / 20 °C

4: K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / dihydroquinidine 1,4-anthraquinonediyl diether / 2-methyl-propan-2-ol; H₂O / 24 h / 4 °C

5: 99 percent / Amberlite IR-120B (H⁺-form) / methanol / 38 h / Heating

6: 95 percent / KOH / methanol / 1 h / Heating

With 1H-imidazole; potassium hydroxide; methanesulfonamide; Amberlite IR-120B (H⁺-form); potassium carbonate; potassium hexacyanoferrate(III); (DHQD)2AQN; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1: Esterification / 2: Condensation / 3: Substitution / 4: Sharpless hydroxylation / 5: Substitution / 6: Hydrolysis;

DOI:10.1271/bbb.63.964

Reference yield:

methyl 2-oxo-3-(4-hydroxyphenyl)propionate (154722-74-4) → (2S,3R)-(+)-piscidic acid (35388-57-9)

Guidance literature:

Multi-step reaction with 5 steps

1: benzene / 2 h / Heating

2: 99 percent / imidazole / dimethylformamide / 5 h / 20 °C

3: K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / dihydroquinidine 1,4-anthraquinonediyl diether / 2-methyl-propan-2-ol; H₂O / 24 h / 4 °C

4: 99 percent / Amberlite IR-120B (H⁺-form) / methanol / 38 h / Heating

5: 95 percent / KOH / methanol / 1 h / Heating

With 1H-imidazole; potassium hydroxide; methanesulfonamide; Amberlite IR-120B (H⁺-form); potassium carbonate; potassium hexacyanoferrate(III); (DHQD)2AQN; In methanol; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1: Condensation / 2: Substitution / 3: Sharpless hydroxylation / 4: Substitution / 5: Hydrolysis;

DOI:10.1271/bbb.63.964

upstream raw materials:

dimethyl (2R,3S)-2,3-dihydroxy-2-(4-hydroxybenzyl)succinate

p-Methoxybenzyl bromide

Lithium; methoxy-[(R)-5-methoxycarbonyl-2,2-dimethyl-[1,3]dioxolan-(4E)-ylidene]-methanolate

4-hydroxyphenylpiruvic acid

Downstream raw materials:

dimethyl (2R,3S)-2,3-dihydroxy-2-(4-hydroxybenzyl)succinate

4'-O-methyl-piscidic acid dimethyl ester

(2R:3S)-2-hydroxy-3-methoxy-2-(4-methoxy-benzyl)-succinic acid dimethyl ester