cas 6283-74-5, (+)-Diacetyl-L-tartaric anhydride

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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.
Raghavan, Vijay,Polavarapu, Prasad L
p. 1629 - 1639
(2017)
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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.
Hoye, Thomas R.,Dvornikovs, Vadims,Sizova, Elena
p. 5191 - 5194
(2006)
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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.
Koike, Kazuo,Yoshino, Hiroshi,Li, Hong-Yu,Sasaki, Tatsunori,Li, Wei
p. 5306 - 5308
(2015)
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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.
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(2019/08/22)

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.
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Paragraph 0130

(2017/08/28)

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.
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(2017/09/27)

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.
Jamaa, Abdelkhalek Ben,Grellepois, Fabienne
p. 10360 - 10375
(2018/05/31)

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.
Hixson, Josh L.,Hayasaka, Yoji,Curtin, Christopher D.,Sefton, Mark A.,Taylor, Dennis K.
p. 9401 - 9411
(2016/12/23)

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.
Liu, Xigong,Meng, Zhilin,Li, Chengkun,Lou, Hongxiang,Liu, Lei
supporting information
p. 6012 - 6015
(2015/05/13)

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.
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Paragraph 0073

(2015/03/16)

Synthesis, antimicrobial and phytotoxic activity of amide derivatives of L-(+)-2,3-diacetoxy-4-methoxy-4-oxo-butanoic acid
A short, versatile, an efficient asymmetric synthesis of substituted aromatic amides is described. L-Tartaric acid conveniently converted into diacetyl-L-tartaric anhydride. Diacetyl-L-tartaric anhydride was then transformed into half ester which was then reacted with substituted anilines to yield respective chiral amides 3-8. These chiral amides were characterized by spectroscopic techniques i.e. 1H-NMR, 13C-NMR, IR and mass spectrometry. Amides 3-8 were tested for their antimicrobial as well as phytotoxic activities.
Malik, Mahrukh,Khan, Sher Wali,Zaidi, Javed Hussain,Khan, Khalid Mohammed,Hussain, Shafqat,Perveen, Shahnaz,Miana, Ghulam Abbas
p. 170 - 176
(2014/05/06)

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.
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(2013/03/26)

Biological evaluation of chiral amides synthesized from diacetyl-L-tartaric acid and aromatic amines
L-Tartaric acid is chiral compound and commercially available was conveniently converted into diacetyl-L-tartaric acid anhydride. Diacetyl- L-tartaric acid anhydride was then made to form half ester of diacetyl-L-tartaric acid anhydride which was then reacted with substituted anilines to yield respected chiral amides. These chiral amides were further purified and were characterized by using 1H NMR. The compound E11 [methyl-2,3-diacetoxy-4-oxo-4-(2'-methoxyphenylamino)butanoate] showed greater antibacterial activity against Staphylococcus aureus and Klebsiella pneumoniae. However, maximum antifungal activity was recorded for E3 [methyl-2, 3-diacetoxy- 4-oxo-4-(4'-bromophenyl amino)butanoate]. The compounds E2 [methyl-2,3- diacetoxy-4-oxo-4-(2'-bromophenyl amino)butanoate] and E3 completely inhibited the germination of canola seeds, whereas, the compounds E1 [methyl-2,3- diacetoxy-4-oxo-4-(4'-methyl phenyl amino)butanoate] and E11 [methyl-2,3-diacetoxy-4-oxo-4-(2'-methoxyphenylamino)butanoate] caused 40 % inhibition of seed germination.
Malik, Mahrukh,Khan, Sher Wali,Arfan, Muhammad,Zaidi, Javid Hussain,Bano, Asghari,Ullah, Faizan
p. 745 - 748
(2013/05/08)

Synthesis of novel succinic acid derivatives as potential matrix metalloproteinases inhibitors and anticancer medicine
In this paper we have designed different methods, according to the differences in nucleophilicity of amino, to conjugate tartaric acid or malic acid with two kinds of useful intermediates respectively via amide bond, envisaging they are promising matrix metalloproteinase inhibitors or anticancer medicine.
Huang, Huiming,Chen, Dan,Li, Shaohua,Liu, Chengmei
scheme or table
p. 155 - 158
(2010/09/15)

Enantioselective addition of boronates to chromene acetals catalyzed by a chiral bronsted acid/lewis acid system
Chiral α ,β-dihydroxy carboxylic acids catalyze the enantioselective addition of alkenyl and aryl boronates to chromene acetals. The optimal carboxylic acid is the easily available tartaric acid amide shown in the scheme. Spectroscopic and kinetic mechanistic studies demonstrate that an exchange process generates a reactive dioxoborolane intermediate leading to enantioselective addition to the pyrylium ion formed from the chromene acetal.
Moquist, Philip N.,Kodama, Tomohiro,Schaus, Scott E.
supporting information; experimental part
p. 7096 - 7100
(2010/11/04)

REAGENTS FOR REVERSIBLY TERMINATING PRIMER EXTENSION
This invention relates to the field of nucleic acid chemistry, more specifically to the field of compositions of matter that comprise triphosphates of modified 2'-deoxynucleosides and oligonucleotides that are formed when these are appended to the 3'-end of a primer, wherein said modifications comprise NH2 moiety attached to their 3'-hydroxyl group and a fluorescent species in a form of a tag affixed to the nucleobase via a linker that can be cleaved. Such compositions and their associated processes enable and improve the sequencing of oligonucleotides using a strategy of cyclic reversible termination, as outlined in US Patent 6,664,079. Most specifically, the invention concerns compositions of matter that are 5'-triphosphates of ribo- and 2'- deoxyribonucleosides carrying detectable tags and oligonucleotides that might be derived from them. The invention also concerns processes wherein a DNA polymerase, RNA polymerase, or reverse transcriptase synthesizes said oligonucleotides via addition of said triphosphates to a primer.
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(2010/11/04)

DERIVATIVES OF SUBSTITUTED TARTARIC ACID AND USAGE FOR PREPARING BETA-SECRETASE INHIBITORS
The present invention relates to compounds represented by formula (I), or isomers, prodrugs, pharmaceutically acceptable salts, solvates or hydrates thereof: in which each substituent of formula (I) is as defined in the specification. The present invention also relates to preparation methods of compounds represented by formula (I), a pharmaceutical composition comprising compounds represented by formula (I) and usage of compounds represented by formula (I) for treating chronic neurodegenerative diseases such as Alzheimer's disease and other diseases induced by aggregation or deposition of β-amyloid peptide.
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(2011/01/05)

Retention of configuration in photolytic decarboxylation of peresters to form chiral acetals and ethers
(Chemical Equation Presented) Peresters generate ethers in good yields when photolyzed in the absence of solvent using short wavelength UV light. At -78 °C or below, the process proceeds predominantly with retention of configuration at the site adjacent to the carbonyl where the decarboxylation occurs, but increase in temperature results in loss of stereochemical control. Chiral acyclic acetals can be prepared using precursors derived from tartaric or malic acids.
Spantulescu, M. Daniel,Boudreau, Marc A.,Vederas, John C.
scheme or table
p. 645 - 648
(2009/09/07)

DERIVATES OF SUBSTITUTED TARTARIC AICD AND USAGE FOR PREPARATING BETA SECRETASE INHIBITORS
The present invention relates to compounds represented by formula (I), or isomers, prodrugs, pharmaceutically acceptable salts, solvates or hydrates thereof: in which each substituent of formula (I) is as defined in the specification. The present invention also relates to preparation methods of compounds represented by formula (I), a pharmaceutical composition comprising compounds represented by formula (I) and usage of compounds represented by formula (I) for treating chronic neurodegenerative diseases such as Alzheimer's disease and other diseases induced by aggregation or deposition of β-amyloid peptide.
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(2009/12/05)

Pyrrolidine N-alkylphosphonates and related nucleotide analogues: synthesis and stereochemistry
N-Phosphonoalkyl-trans-3,4-dihydroxypyrrolidine derivatives were synthesized and exploited as synthons for the preparation of hydroxypyrrolidine nucleoside phosphonic acids, the 3′-deoxynucleoside 5′-phosphate analogues. Simultaneously, an alternative route, the N-phosphoalkylation of the preformed pyrrolidine nucleosides employing Mannich- and Michael-type reactions, was investigated to obtain desired nucleotide analogues. In contrast to the latter approach, the former resulted in the formation of two diastereoisomers very likely due to the existence of two possible SN2 transition states during a nucleophilic displacement. The stereochemistry of the prepared nucleotide analogues was studied by NMR spectroscopy.
Rejman, Dominik,Pohl, Radek,Ko?alka, Petr,Masojídková, Milena,Rosenberg, Ivan
scheme or table
p. 3673 - 3681
(2009/09/30)

Nucleophilic addition of potassium organotrifluoroborates to chiral cyclic N-acyliminium ions: stereoselective synthesis of functionalized N-heterocycles
The stereoselective nucleophilic addition of potassium aryl- and alkynyltrifluoroborates to cyclic N-acyliminium ion derivatives from N-benzyl-3,4,5-triacetoxy-2-pyrrolidinone, affording the respective 5-substituted 2-pyrrolidinone is described. The products were obtained in moderate to good yields and with preference for the syn diastereomer.
Vieira, Adriano S.,Ferreira, Fernando P.,Fiorante, Pedro F.,Guadagnin, Rafael C.,Stefani, Hélio A.
p. 3306 - 3314
(2008/09/21)

O-(2-oxopyrrolidin-5-yl)trichloroacetimidates as amidoalkylating agents - Synthesis of (+)-lentiginosine
N-α-Hydroxyalkylamides 6a,b, readily available from L-tartrate, with trichloroacetonitrile furnish O-(2-oxopyrrolidin-5-yl)trichloroacetimidates 3a,b. α-Amido-alkylation studies of 3a,b with allyl-trimethylsilane and electron-rich benzene derivatives as C-nucleophiles afforded 5-allyl- and 5-aryl-2-pyrrolidinones 2a,b, 7a,b, and 8-10. The target compound (+)-1 and its epimer 15 were readily obtained from 1,5-diallyl-2-pyrrolidinones 2b and 7b, respectively, via ring-closing metathesis, amide group reduction, and CC-double bond hydrogenation. Wiley-VCH Verlag GmbH & Co KGaA, 69451 Weinheim, Germany, 2002.
El-Nezhawy, Ahmed O. H.,El-Diwani, Hoda I.,Schmidt, Richard R.
p. 4137 - 4142
(2007/10/03)

New route to enantiomers of cyclic β-hydroxyethers. The crystal structure of (S)-(+)-tetrahydrofurfuryl-O,O'-diacetyl-(2R,3R)-hydrogentartrate
Title compounds 1-2 were readily resolved into their enantiomers by crystallizing their half esters formed with O,O'-diacetyl-(2R,3R)-tartaric acid. An intermolecular H-bond between the free carboxyl group and the ring oxygen, determined by single crystal X-ray study of (S)-(+)-tetrahydrofurfuryl-O,O'-diacetyl-(2R,3R)-hydrogentartrate, enhances the selectivity and the crystallizing ability itself.
Mravik, Andras,Boecskei, Zsolt,Keszei, Sandor,Elekes, Ferenc,Fogassy, Elemer
p. 1477 - 1484
(2007/10/03)

Novel 2-chrysenyl- and 1-pyrenyl-tartaramide derivatives as liquid chromatographic chiral phases for enantiomeric separation on porous graphitic carbon
Four new chiral stationary phases have been obtained by coupling 2-chrysenyl-amine and 1-pyrenylamine to chiral selector groups based on (R,R)-tartaric acid diamide. The compounds (R,R)-N-isopropyl-N'-(1-pyrenyl)tartaramide, (R,R)-N-(2-chrysenyl)-N'-isopropyltartaramide and (R,R)-N-(2-chrysenyl)-N'-(3-nitrophenyl)tartaramide are strongly adsorbed on to porous graphitic carbon to produce a novel type of carbon-based chiral stationary phase. These new materials were evaluated by HPLC and were found to exhibit excellent enantioselectivity for various types of compound including aromatic alcohols, binaphthyl derivatives, β-blocking agents and anti-inflammatory agents. These new chiral phases are very stable showing negligible tendency for phase loss or degradation.
Monser, Lotfi I.,Greenway, Gillian M.,Ewing, David F.
p. 1189 - 1198
(2007/10/03)

Practical synthesis of (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione and its acetate from L-tartaric acid
An efficient method for preparing (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione and its acetate is described starting from L-tartaric acid, which affords the desired compounds with 99% ee in good overall yields (63-74%).
Tomori, Hiroshi,Maruyama, Hiroshi,Ogura, Katsuyuki
p. 415 - 423
(2007/10/03)

Enantioenriched N-(2-Chloroalkyl)-3-acetoxypiperidines as Potential Cholinotoxic Agents. Synthesis and Preliminary Evidence for Spirocyclic Aziridinium Formation.
The syntheses of six enantioenriched analogs representing cyclic forms of acetylcholine are reported. (S)- and (R)-N-(2-chloroethyl)-3-acetoxypiperidine and (R,R)-, (R,S)-, (S,R)-, and (S,S)-N-(2-chloropropyl)-3-acetoxypiperidine have been synthesized from (R)- or (S)-3-hydroxypiperidine in five steps. (R)- and (S)-3-hydroxypiperidine were accessed via parallel stereospecific routes from d- and l-glutamic acid, and through fractional recrystallization of diastereomeric tartranilic acid salts. (S)-N-(2-Chloroethyl)-3-acetoxypiperidine was reacted with silver perchlorate to form a spirocyclic aziridinium analog of acetylcholine as evidenced by a characteristic 1H NMR shift for the aziridinium methylene groups.
Huh, Nam,Thompson, Charles M.
p. 5935 - 5950
(2007/10/02)

A Chiral Stationary Phase Derived from (R,R)-Tartramide with Broadened Scope of Application to the Liquid Chromatographic Resolution of Enantiomers
An understanding of the retention process of solute enantiomers on a chiral stationary phase (CSP) would indicate the importance of eliminating the nonenantioselective, i.e., solute-silanol, interaction that occurs in this process.For clarification of this matter, a CSP in which a (R,R)-N,N'-dialkyltartramide derivative is linked to the silica gel surface via 11 methylene units and the remaining silanol groups are trimethylsilylated was synthesized.This CSP was found capable of chiral recognition of broad categories of enantiomers containing α- or β-hydroxycarbonyl, α-amino acid, β-aminoalcohol, primary amine derivatives, barbiturates, glutarimide, α-hydroxy ketoximes, carbinols, 1,2-diols, and bi-β-naphthol.The driving force to bring about enantioselective association is ascribable to hydrogen bonding.The effects of a reduction in the number of remaining silanol groups on CSP and a long alkyl chain as a linkage of the tetramide moiety to CSP are discussed on the basis of retentivity of enantiomers.
Dobashi, Yasuo,Hara, Shoji
p. 2490 - 2496
(2007/10/02)