Butanedioic acid, 2,3-bis[(4-methylbenzoyl)oxy]-, (2S,3S)-

Base Information

• Chemical Name: Butanedioic acid, 2,3-bis[(4-methylbenzoyl)oxy]-, (2S,3S)-
• CAS No.: 32634-68-7
• Deprecated CAS: 139159-61-8,47586-11-8,79780-71-5,79881-62-2,1624984-70-8
• Molecular Formula: C20H18O8
• Molecular Weight: 386.358
• Hs Code.: 29181300
• European Community (EC) Number: 251-132-2
• NSC Number: 97592
• UNII: 4480MA5QIP
• DSSTox Substance ID: DTXSID80885539
• Nikkaji Number: J208.350G
• Wikidata: Q27258721
• ChEMBL ID: CHEMBL1490343
• Mol file: 32634-68-7.mol

Synonyms:di-p-toluoyl-D-tartaric acid;di-p-toluoyltartaric acid

Chemical Property of Butanedioic acid, 2,3-bis[(4-methylbenzoyl)oxy]-, (2S,3S)-

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 169-171 °C(lit.)
• Refractive Index: 139 ° (C=1, EtOH)
• Boiling Point: 626.5 °C at 760 mmHg
• PKA: 1.46±0.25(Predicted)
• Flash Point: 223.2 °C
• PSA: 127.20000
• Density: 1.371 g/cm³
• LogP: 2.22360
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Ethanol (Sparingly), Methanol (Slightly)
• Water Solubility.: 112.55mg/L at 25℃
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 386.10016753
• Heavy Atom Count: 28
• Complexity: 533

Purity/Quality:

99% ^*data from raw suppliers

(+)-O,O′-Di-p-toluoyl-D-tartaric acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36/37-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC1=CC=C(C=C1)C(=O)OC(C(C(=O)O)OC(=O)C2=CC=C(C=C2)C)C(=O)O
• Isomeric SMILES: CC1=CC=C(C=C1)C(=O)O[C@@H]([C@@H](C(=O)O)OC(=O)C2=CC=C(C=C2)C)C(=O)O
• Uses: blood volume expander Inhibitor of enzyme. Rivastigmine USP Related Compound A.

Technology Process of Butanedioic acid, 2,3-bis[(4-methylbenzoyl)oxy]-, (2S,3S)-

There total 8 articles about Butanedioic acid, 2,3-bis[(4-methylbenzoyl)oxy]-, (2S,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:

rac-O,O'-di-p-toluoyltartaric acid (32634-66-5,32634-68-7,100168-11-4,104528-81-6) → Di-p-toluoyl-L-tartaric acid (32634-66-5) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7)

Guidance literature:

With C₂₂H₂₄N₂⁽²⁺⁾*2CF₃O₃S^(1-); In aq. acetate buffer; at 20 ℃; pH=8.1; Resolution of racemate;

DOI:10.1002/chem.201800369

Reference yield:

(3S,4S)-2,5-dioxotetrahydrofuran-3,4-diyl bis(4-methylbenzoate) (72842-25-2,156835-63-1) → (2S,3S)-di-4-toluoyltartaric acid (32634-68-7)

Guidance literature:

With water; In toluene; for 5h; Reflux; Large scale;

Reference yield:

(R)-2-cyclopropylaminocyclohexanol di-p-toluoyl-D-tartrate (339546-21-3) → (R)-2-cyclopropylaminocyclohexanol (339546-20-2) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7)

Guidance literature:

With sodium hydroxide; In water; at 20 - 30 ℃; for 1h; Product distribution / selectivity;

upstream raw materials:

rac-O,O'-di-p-toluoyltartaric acid

(R)-2-cyclopropylaminocyclohexanol di-p-toluoyl-D-tartrate

(3S,4S)-2,5-dioxotetrahydrofuran-3,4-diyl bis(4-methylbenzoate)

Downstream raw materials:

l-nicotine di-(p-toluoyl)-d-tartrate

2C₁₆H₂₅NO₃*C₂₀H₁₈O₈

Refernces

• 1、 -. "A D-P-methyl-dibenzoyl tartaric acid synthesis method (by machine translation)". Paragraph 0034-0036. . Retrieved 2017/03/08.
• 2、 -. "PROCESSES FOR THE RECOVERY OF OPTICALLY ACTIVE DIACYLTARTATIC ACIDS". Page/Page column 6-9. . Retrieved 2008/06/13.