6283-74-5

Usage

Uses

Used in Pharmaceutical Analysis:
(+)-Diacetyl-L-tartaric anhydride is used as a chiral derivatizing agent for the determination of enantiomeric vigabatrin in mouse serum samples. This application is crucial in pharmaceutical analysis, as it allows for the accurate measurement and differentiation of the two enantiomers of vigabatrin, which can have different biological activities and effects.
(+)-Diacetyl-L-tartaric anhydride is used as a chiral derivatizing agent for the determination of trantinterol in rat plasma by ultra-performance liquid chromatography–electrospray ionization mass spectrometry (UPLC–MS/MS). This technique is essential in the development and monitoring of pharmaceutical drugs, as it enables the precise measurement of drug concentrations in biological samples, ensuring the safety and efficacy of the drug.
Used in Organic Synthesis:
(+)-Diacetyl-L-tartaric anhydride is a compound useful in organic synthesis, where it can be employed as a building block or intermediate in the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable component in the creation of complex molecules and pharmaceuticals.

Purification Methods

If the IR is good, i.e. no OH bands, then keep it in a vacuum desiccator overnight (over P2O5/paraffin) before use. If OH bands are present then reflux 4g in Ac2O (12.6mL) containing a few drops of conc H2SO4 for 10minutes (use a relatively large flask), pour onto ice, collect the crystals, wash with dry *C6H6 (2 x 2mL), stir with 17mL of cold Et2O, filter and dry in it a vacuum desiccator as above, or store it in dark evacuated ampoules under N2 in small aliquots. It is not very stable in air, the melting point of the crystals drop one degree in the first four days then remains constant (132-134o). If placed in a stoppered bottle, it becomes gummy and the m falls 100o in three days. Recrystllisation leads to decomposition. If good quality anhydride is required it, should be prepared freshly from tartaric acid. It sublimes in a CO2 atmosphere. [Shriner & Furrow Org Synth Coll Vol IV 242 1963, Bell Aust J Chem 34 671 1981, Beilstein 18 III/IV 2296.]

InChI:InChI=1/C8H8O7/c1-3(9)13-5-6(14-4(2)10)8(12)15-7(5)11/h5-6H,1-2H3/t5-,6-/m1/s1

Upstream product

• 87-69-4 L-Tartaric acid 
• 108-24-7 acetic anhydride 
• 147-71-7 D-tartaric acid 
• 87-69-4 tartaric acid 
• 75-36-5 acetyl chloride 

Downstream Products

• 106942-29-4 L_g-tartaric acid di-p-toluidide 
• 6249-84-9 N-(4-sulfamoyl-phenyl)-L_g-tartramic acid 
• 3019-58-7 N-phenyl-L_g-tartramic acid 
• 78814-80-9 O-benzyl diacetoxysuccinohydroxamate 
• 115061-72-8 phenylammonium salt of (2R,3R)-3-acetoxy-2-hydroxy-3-(phenylcarbamoyl)propanoic acid 
• 115061-70-6 benzylammonium salt of (2R,3R)-3-acetoxy-3-benzylcarbamoyl-2-hydroxypropanoic acid 
• 115061-64-8 benzylammonium salt of (2R,3R)-2,3-diacetoxy-3-(benzylcarbamoyl)propanoic acid 
• 123524-99-2 benzyl diacetoxysuccinic acid 
• 17447-35-7 (R,R)-(+)-4-chlorotartranilic acid 
• 115061-63-7 (2R,3R)-2,3-diacetoxy-4-(benzylamino)-4-oxobutanoic acid 
• 164027-62-7 (R,R)-N-(3-nitrophenyl)-O,O-diacetyltartaric acid monoamide 
• 1056614-85-7 C₂₂H₂₃NO₇ 
• 1305349-49-8 C₁₇H₂₁NO₇ 
• 1305349-48-7 C₁₇H₂₁NO₇ 

Relevant academic research and scientific papers

First Room Temperature Chiral Anionic Liquid Forming Micelles and Reverse Micelles

We report the first chiral surface active anionic liquid, T12M, derived from biodegradable tartaric acid, and its unusual properties. T12M features unprecedented combination of characteristics not found in other ionic liquids (ILs): (a) T12M is the first surface active ionic liquid that is fully chiral, by virtue of the presence of chirality in both anionic headgroup and the counterion; (b) T12M remains as room temperature IL for 3 days and then transforms to a semisolid with melting point at ～55 °C. The d-spacings in solid T12M, and T12M lyophilized from its aqueous solution, are 13.89 and 14.54 ?, respectively. (c) Tartaric acid is unconventional and unprecedented starting material for the synthesis of ILs. (d) T12M dissolves in both hydrogen bonding (water) and non-hydrogen bonding (chloroform) solvents and forms anionic chiral micellar aggregates (CMAs) and reverse-CMAs, at very low concentrations 0.32 mM and ～10 mM, respectively. (e) CMAs of T12M adopt structures ranging from spherical to lamellar in shape in water in the 10-200 mM range; however, the zeta potential remained constant at ～ -13 mV. The alkyl chains, are interdigited in the CMAs of T12M in water to form lamellar structures and are extended outward to form reverse micelles in CHCl3.

Silylative Dieckmann-like cyclizations of ester-lmides (and diesters)

Trialkylsilyl triflates effect cyclization of ester-imides such as 2 to produce adducts such as 4a. Trapping of the in situ generated, nucleophilic ketene acetal (cf. 5a) is a key aspect of the transformation. A range of substrates amenable to this operationally simple reaction is reported. In many instances the levels of diastereoselectivity are very high. Mechanistic points are inferred from spectroscopic observations.

Determination of the absolute configuration of picrasidine Y, a naturally occurring β-carboline alkaloid

Abstract The absolute configuration of picrasidine Y, a β-carboline alkaloid isolated from Picrasma quassioides (Simaroubaceae), has not been determined. To determine the absolute configuration of picrasidine Y, we synthesized stereoisomers of picrasidine Y through 7-step chemical reactions using tartaric acid as a starting material. Moreover, we extended the scope of application of this synthetic method to canthin-5,6-dione compounds. The absolute configuration of natural picrasidine Y was elucidated based on comparisons of chemically synthesized isoforms with the naturally occurring compound in 1H and 13C NMR spectra, specific optical rotation, HPLC analysis with chiral columns, computational molecular simulation, and analysis with the CD exciton chirality method.

SURFACE ACTIVE IONIC LIQUID WITH ACTIVITY IN AQUEOUS AND NON-AQUEOUS MEDIA

Disclosed herein are surfactant compounds, that are surface active, liquid, chiral, and micelle forming. Also disclose herein are ionic liquids and compsitions comprising the surfactant compounds.

Diastereoselective ritter-like reaction on cyclic trifluoromethylated N,O-acetals derived from L-tartaric acid

Despite the presence of the highly electron-withdrawing fluorinated substituent, cyclic α-trifluoromethylated N-acyliminium ions were successfully generated from fluorinated O-acetyl-N,O-acetal L-tartaric acid derivatives. The addition of nitriles on these intermediates occurred with high to excellent syn diastereoselectivity and led, in most cases, to oxazolines and amides as single diastereomers. The diastereoselectivity of the addition and the nature of the reaction product depend on the substituents on the hydroxyl groups of the tartaric acid scaffold. This methodology gave access to enantiopure, highly functionalized 5-(trifluoromethyl)pyrrolidin-2-one derivatives, bearing the fluorinated substituent on a tetrasubstituted carbon.

Brain-targeting eslicarbazepine ester prodrug and application thereof

The invention relates to an eslicarbazepine ester prodrug and an application thereof, wherein the prodrug is a compound represented by the formula (I) or optical isomers or physiologically acceptable salts of the compound represented by the formula (I), wherein R represents a lipophilic substituent. The compound represented by the formula (I) is the eslicarbazepine ester prodrug containing the lipophilic substituent, is converted into eslicarbazepine through metabolism in vivo to play pharmacological effects, and can be applied in preparation of drugs for treatment, prevention or adjuvant treatment of central nervous system diseases, such as epilepsy and the like.

RESVERATROL GLYCOLATE AND TARTRATE DERIVATIVES AND SYNTHETIC METHODS THEREFOR

The invention is in the field of resveratrol derivative compounds and compositions, and methods for synthesizing same.

Hydroxycinnamoyl Glucose and Tartrate Esters and Their Role in the Formation of Ethylphenols in Wine

Synthesized p-coumaroyl and feruloyl l-tartrate esters were submitted to Brettanomyces bruxellensis strains AWRI 1499, AWRI 1608, and AWRI 1613 to assess their role as precursors to ethylphenols in wine. No evolution of ethylphenols was observed. Additionally, p-coumaroyl and feruloyl glucose were synthesized and submitted to B. bruxellensis AWRI 1499, which yielded both 4-ethylphenol and 4-ethylguaiacol. Unexpected chemical transformations of the hydroxycinnamoyl glucose esters during preparation were investigated to prevent these in subsequent synthetic attempts. Photoisomerization gave an isomeric mixture containing the trans-esters and undesired cis-esters, and acyl migration resulted in a mixture of the desired 1-O-β-ester and two additional migrated forms, the 2-O-α- and 6-O-α-esters. Theoretical studies indicated that the photoisomerization was facilitated by deprotonation of the phenol, and acyl migration is favored during acidic, nonaqueous handling. Preliminary LC-MS/MS studies observed the migrated hydroxycinnamoyl glucose esters in wine and allowed for identification of feruloyl glucose in red wine for the first time.

Organocatalytic enantioselective oxidative C-H alkenylation and arylation of N-Carbamoyl tetrahydropyridines and tetrahydro-β-carbolines

The first organocatalytic enantioselective C-H alkenylation and arylation reactions of N-carbamoyl tetrahydropyridines and tetrahydro-β-carbolines (THCs) are described. The metal-free processes represent an efficient and straightforward approach to a variety of structurally and electronically diverse α-substituted tetrahydropyridines and THCs in good yields with excellent regio- and enantioselectivities. Preliminary control experiments provide important insights into the reaction mechanism.

PROCESS FOR THE PREPARATION AND PURIFICATION OF ESLICARBAZEPINE ACETATE AND INTERMEDIATES THEREOF

The present invention provides a novel process for the preparation of 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide, commonly known as oxcarbazepine, which is a medicament and a useful intermediate in the preparation of eslicarbazepine acetate. The present invention further provides a process for the preparation and purification of eslicarbazepine acetate.