di-p-Toluoyl-L-tartaric acid

Base Information

• Chemical Name: di-p-Toluoyl-L-tartaric acid
• CAS No.: 32634-66-5
• Molecular Formula: C20H18O8
• Molecular Weight: 386.358
• Hs Code.: 29181300
• European Community (EC) Number: 251-131-7
• UNII: DH4M72TU6M
• DSSTox Substance ID: DTXSID20885538
• Nikkaji Number: J208.347G
• Wikidata: Q72469493
• Mol file: 32634-66-5.mol

Synonyms:32634-66-5;di-p-Toluoyl-L-tartaric acid;(2R,3R)-2,3-Bis((4-methylbenzoyl)oxy)succinic acid;(-)-O,O'-Di-p-toluoyl-L-tartaric acid;(-)-Di-p-toluoyl-L-tartaric acid;(2R,3R)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid;MFCD00064440;(-)-di-1,4-o-toluoyl-l-tartaric acid;2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid;C20H18O8;Butanedioic acid, 2,3-bis[(4-methylbenzoyl)oxy]-, (2R,3R)-;217968-14-4;Butanedioic acid, 2,3-bis((4-methylbenzoyl)oxy)-, (2R,3R)-;EINECS 251-131-7;Butanedioic acid, 2,3-bis[(4-methylbenzoyl)oxy]-, [R-(R*,R*)]-;l-dtta;di-p-Toluoyl-L-tartaricacid;[R(R*,R*)]-2,3-bis[(4-methylbenzoyl)oxy]succinic acid;DH4M72TU6M;Tartaric acid, di-p-toluate;SCHEMBL72171;Butanedioic acid, 2,3-bis((4-methylbenzoyl)oxy)-, (R-(R*,R*))-;(2R,3R)-2,3-bis(4-methylbenzoyloxy)butanedioic acid;L-(-)-DTTA;DTXSID20885538;CMIBUZBMZCBCAT-HZPDHXFCSA-N;L-(-)-di-p-Toluoyltartaric acid;(?)-Bis(p-toluoyl)-L-tartaric acid;AKOS016842466;Di-p-toluoyl-L-tartaric acid, (-)-;AC-3432;AM81409;AS-12034;CS-0015300;D1387;EN300-155387;(-)-O,O'-Di-p-toluoyl-L-tartaric acid, 97%;(2r,3r)-2,3-bis(4-methylbenzoyloxy)succinic acid;W-106833;F0001-0969;(-)-O,O'-Di-p-toluoyl-L-tartaric acid, purum, >=98.0% (T);(2r,3r)-(-)-2,3-bis[(4-methylbenzoyl)oxy]butane-1,4-dioic acid

Chemical Property of di-p-Toluoyl-L-tartaric acid

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: 136.43000
• Density: 1.371 g/cm³
• LogP: 2.15930
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• Water Solubility.: soluble
• 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-L-tartaricAcid ^*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:

• 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: (-)-di-p-toluoyl-l-tartaric acid can be used as a chiral resolving agent for the resolution of the racemic bases to isolate the (-)-enantiomeric forms. Escitalopram intermediate (-)-O,O’-Di-p-toluoyl-L-tartaric Acid is a useful reagent for the preparation of the upadacitinib salt compound. Inhibitor of enzyme

Technology Process of di-p-Toluoyl-L-tartaric acid

There total 9 articles about di-p-Toluoyl-L-tartaric 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:

3-aminomethyl-5-methylhexanoic acid (-)-(O,O')-di-p-toluoyl-L-tartaric acid salt → Di-p-toluoyl-L-tartaric acid (32634-66-5)

Guidance literature:

In tetrahydrofuran; water; at 30 ℃; for 2.33333 - 3h;

Reference yield:

C10H14N2*C20H18O8 → Di-p-toluoyl-L-tartaric acid (32634-66-5)

Guidance literature:

With hydrogenchloride; In tert-butyl methyl ether; water; for 0.5h;

Reference yield:

L-Tartaric acid (87-69-4,138508-61-9) + 4-methyl-benzoyl chloride (874-60-2) → Di-p-toluoyl-L-tartaric acid (32634-66-5)

Guidance literature:

at 170 ℃; for 1h;

upstream raw materials:

di-O-p-toluoyl-L-threaric acid-anhydride

L-Tartaric acid

4-methyl-benzoyl chloride

(R)-α-(2,3-dimethoxyphenyl)-4-piperidinemethanol, (2R,3R)-(-)-di-(p-toluoyl)tartaric acid salt

Downstream raw materials:

1-benzo[1,3]dioxol-5-yl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline; O²,O³-bis-(4-methyl-benzoyl)-L_g-tartrate (1:1)

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

(+)-nicotine-(+)-di-p-toluoyltartrate

Refernces

Resolution of 1-n-butyl-3-methyl-3-phospholene 1-oxide with TADDOL derivatives and calcium salts of O,O'-dibenzoyl-(2R,3R)- or O,O'-di-p-toluoyl- (2R,3R)-tartaric acid

10.1002/chir.22293

The research aimed to develop resolution methods for the preparation of optically active 1-n-butyl-3-methyl-3-phospholene 1-oxide, a compound of interest in organic chemistry due to its potential use in enantioselective catalysis. The study employed TADDOL derivatives and calcium salts of O,O’-dibenzoyl-(2R,3R)- or O,O’-di-p-toluoyl-(2R,3R)-tartaric acid as resolving agents. Through various procedures, both enantiomers of the phospholene oxide were prepared with high enantiomeric excess (ee >95%). The absolute P-configuration of the enantiomers was determined using X-ray crystallography and CD spectroscopy with quantum chemical calculations. The research concluded that the solvents significantly influenced the efficiency of the resolutions, and the different antipode preference of TADDOL derivatives in various solvents was exploited to obtain both enantiomers. The study also revealed the inherent mobility of these P-heterocycles and their interactions with resolving agents.

Chiral resolution, absolute configuration determination, and stereo-activity relationship study of IDO1 inhibitor NLG919

10.1016/j.tet.2018.05.005

The research focuses on the development of an effective method to prepare optically pure stereoisomers of the IDO1 inhibitor NLG919. The study involves the chiral resolution of the racemic intermediate 2 using di-p-toluoyl-L-tartaric acid (L-7) in a dichloromethane and n-pentane solvent system. The absolute configurations of the stereoisomers were determined through electronic circular dichroism (ECD) spectra, quantum-chemical calculations, and transition metal methods. The pharmacological evaluation revealed that the S configuration at the C5 position is crucial for the IDO1 inhibitory activity, while the stereochemistry at the C2’ position has less impact.