Production Method 1

1917354-49-4

6968-76-9

32634-68-7

917389-29-8

Reaction Conditions

1.1 Reagents: Phosphorus pentachloride Solvents: Toluene

Reference

Asymmetric Synthesis of Letermovir Using a Novel Phase-Transfer-Catalyzed Aza-Michael Reaction

Humphrey, Guy R.; et al, Organic Process Research & Development, 2016, 20(6), 1097-1103

Production Method 2

917389-29-8

32634-68-7

32634-68-7

917389-29-8

Reaction Conditions

1.1 Solvents: Ethyl acetate ;  rt → 45 °C; 2 h, 45 °C
1.2 Reagents: Ethyl acetate ;  45 °C → rt; 3 h, rt

Reference

Asymmetric Synthesis of Letermovir Using a Novel Phase-Transfer-Catalyzed Aza-Michael Reaction

Humphrey, Guy R.; et al, Organic Process Research & Development, 2016, 20(6), 1097-1103

Production Method 3

69-72-7

32634-68-7

1791412-04-8

32634-68-7

917389-29-8

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Solvents: Toluene ,  Water ;  rt → 45 °C; 1 h, 45 °C
1.2 Reagents: Tripotassium phosphate Catalysts: Cinchonanium, 1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-9-hydroxy-1′-[[3-(trifl… Solvents: Dimethylformamide ;  45 °C → 0 °C; 5 h, 0 °C
1.3 Reagents: Glycolic acid ;  0 °C → 50 °C; 2 h, 50 °C
1.4 Reagents: Ethyl acetate Solvents: Toluene ;  rt → 45 °C; 2 h, 45 °C

Reference

Asymmetric Synthesis of Letermovir Using a Novel Phase-Transfer-Catalyzed Aza-Michael Reaction

Humphrey, Guy R.; et al, Organic Process Research & Development, 2016, 20(6), 1097-1103

(+)-O,O’-Di-p-toluoyl-D-tartaric Acid Raw materials

• Salicylic acid
• 4-Quinazolineacetic acid, 8-fluoro-1,2,3,4-tetrahydro-3-[2-methoxy-5-(trifluoromethyl)phenyl]-2-oxo-, methyl ester, (4S)-
• 4-Quinazolineacetic acid, 8-fluoro-3,4-dihydro-2-[4-(3-methoxyphenyl)-1-piperazinyl]-3-[2-methoxy-5-(trifluoromethyl)phenyl]-, methyl ester
• (+)-O,O’-Di-p-toluoyl-D-tartaric Acid
• 1-(3-Methoxyphenyl)piperazine dihydrochloride
• methyl (E)-3-(3-fluoro-2-(((E)-((2-methoxy-5-(trifluoromethyl)phenyl)amino)(4-(3-methoxyphenyl)piperazin-1-yl)methylene)amino)phenyl)acrylate

(+)-O,O’-Di-p-toluoyl-D-tartaric Acid Preparation Products

• 4-Quinazolineacetic acid, 8-fluoro-3,4-dihydro-2-[4-(3-methoxyphenyl)-1-piperazinyl]-3-[2-methoxy-5-(trifluoromethyl)phenyl]-, methyl ester (917389-29-8)
• (+)-O,O’-Di-p-toluoyl-D-tartaric Acid (32634-68-7)

• 1. Enantiopure methoxetamine stereoisomers: chiral resolution, conformational analysis, UV-circular dichroism spectroscopy and electronic circular dichroism
  Kun Won Lee,Ahmed H. E. Hassan,Youngdo Jeong,Seolmin Yoon,Seung-Hwan Kim,Cheol Jung Lee,Hye Rim Jeon,Suk Woo Chang,Ji-Young Kim,Dae Sik Jang,Hee Jin Kim,Jae Hoon Cheong,Yong Sup Lee New J. Chem. 2021 45 4354
• 2. Isolation and structural determination of non-racemic tertiary cathinone derivatives
  M.-J. Zhou,S. Bouazzaoui,L. E. Jones,P. Goodrich,S. E. J. Bell,G. N. Sheldrake,P. N. Horton,S. J. Coles,N. C. Fletcher Org. Biomol. Chem. 2015 13 9629
• 3. Concise asymmetric synthesis of a (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid-derived sulfonamide and ethyl ester
  Sha Lou,Nicolas Cuniere,Bao-Ning Su,Lindsay A. Hobson Org. Biomol. Chem. 2013 11 6796
• 4. Diastereomeric salts of (S,S)-sertraline with l- and d-tartaric acids: an investigation into chiral supramolecular discrimination
  Paulo S. Carvalho,Luan F. Diniz,Alejandro P. Ayala CrystEngComm 2023 25 1693
• 5. Synthesis and pharmacological effects of the enantiomers of the N-phenethyl analogues of the ortho and para e- and f-oxide-bridged phenylmorphans
  Josef Zezula,Lisa Singer,Anna K. Przyby?,Akihiro Hashimoto,Christina M. Dersch,Richard B. Rothman,Jeffrey Deschamps,Yong Sok Lee,Arthur E. Jacobson,Kenner C. Rice Org. Biomol. Chem. 2008 6 2868

• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Tetracarboxylic acids and derivatives

Professional Introduction to (+)-O,O’-Di-p-toluoyl-D-tartaric Acid (CAS No. 32634-68-7)

(+)-O,O’-Di-p-toluoyl-D-tartaric Acid is a specialized organic compound that has garnered significant attention in the field of chemical and pharmaceutical research. This compound, identified by its CAS number 32634-68-7, is a derivative of tartaric acid, which is well-known for its chiral properties and its role in various biochemical processes. The introduction of p-toluate groups at the oxygen positions enhances its utility in synthetic chemistry and pharmaceutical applications.

The structural configuration of (+)-O,O’-Di-p-toluoyl-D-tartaric Acid is characterized by the presence of two p-toluate esters linked to the D-tartaric acid backbone. This unique structure imparts distinct chemical and biological properties, making it a valuable intermediate in the synthesis of complex molecules. The compound’s stereochemistry, specifically the D configuration of tartaric acid, plays a crucial role in its interactions with biological targets, which has been a focus of recent research.

In recent years, (+)-O,O’-Di-p-toluoyl-D-tartaric Acid has been explored for its potential in drug development. Its chiral nature makes it an excellent candidate for creating enantiomerically pure compounds, which are often required in pharmaceutical formulations to ensure efficacy and minimize side effects. The compound’s ability to act as a chiral auxiliary in asymmetric synthesis has been particularly noteworthy, enabling the production of enantiomerically enriched intermediates for various therapeutic agents.

One of the most promising applications of (+)-O,O’-Di-p-toluoyl-D-tartaric Acid lies in its use as a building block for more complex molecules. Researchers have leveraged its structural features to develop novel inhibitors targeting specific enzymes involved in metabolic pathways. For instance, studies have demonstrated its utility in synthesizing potent inhibitors of α-glucosidase, an enzyme implicated in diabetes management. The compound’s ability to modulate enzyme activity without significant off-target effects makes it an attractive scaffold for further derivatization.

The synthesis of (+)-O,O’-Di-p-toluoyl-D-tartaric Acid involves multi-step organic reactions that highlight the compound’s synthetic versatility. The process typically begins with the esterification of tartaric acid derivatives followed by selective acylation with p-tolyl chlorides. Advanced synthetic methodologies, such as catalytic asymmetric reactions, have been employed to improve yield and purity. These advancements underscore the growing importance of this compound in fine chemical synthesis.

Recent research has also explored the pharmacological properties of (+)-O,O’-Di-p-toluoyl-D-tartaric Acid beyond its role as a synthetic intermediate. Studies have indicated that it may possess anti-inflammatory and antioxidant properties, which could be harnessed for therapeutic applications. The compound’s interaction with biological systems has been investigated using computational modeling and experimental techniques, providing insights into its mechanism of action.

The industrial significance of (+)-O,O’-Di-p-toluoyl-D-tartaric Acid is further emphasized by its incorporation into various drug formulations under development. Its stability under different conditions and compatibility with other pharmaceutical excipients make it a preferred choice for formulation scientists. As regulatory agencies continue to approve new drugs based on chiral intermediates, the demand for high-quality sources like this compound is expected to rise.

Future research directions for (+)-O,O’-Di-p-toluoyl-D-tartaric Acid include exploring its potential in green chemistry initiatives. Efforts are underway to develop more sustainable synthetic routes that minimize waste and reduce environmental impact. Additionally, investigating its role in combination therapies could uncover novel therapeutic strategies with enhanced efficacy and reduced toxicity.

In conclusion, (+)-O,O’-Di-p-toluoyl-D-tartaric Acid (CAS No. 32634-68-7) is a multifaceted compound with significant implications in chemical synthesis and pharmaceutical development. Its unique structural features and versatile applications make it a cornerstone in modern drug discovery efforts. As research continues to uncover new possibilities, this compound is poised to play an even greater role in advancing medical science.

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