608-68-4

Basic information

• Product Name: (+)-Dimethyl L-tartrate
• Synonyms: (+)-TARTARIC ACID DIMETHYL ESTER;2,3-dihydroxy-[theta-(theta,theta)]-butanedioicacidimethylester;DimethylL-(+)-tartarate;Lg-tartaricaciddimethylester;(2R,3R)-(+)-DIMETHYL TARTRATE;(2R,3R)-2,3-DIHYDROXY-SUCCINIC ACID DIMETHYL ESTER;(+)-DIMETHYL TARTRATE;DIMETHYL (2R,3R)-DIHYDROXYSUCCINATE
• CAS NO: 608-68-4
• Molecular Formula: C₆H₁₀O₆
• Molecular Weight: 178.14
• EINECS: 210-166-8
• Product Categories: FINE Chemical & INTERMEDIATES;Chiral Compounds;chiral;Chiral Building Blocks;Esters (Chiral);Synthetic Organic Chemistry;CHIRAL CHEMICALS;Hydroxy Acids & Deriv.;Chiral Compound
• Mol File: 608-68-4.mol

Chemical Properties

• Melting Point: 57-60 °C (dec.)(lit.)
• Boiling Point: 163 °C23 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White/Crystals
• Density: 1.238 g/mL at 25 °C(lit.)
• Refractive Index: 21 ° (C=2.5, H2O)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 11.44±0.20(Predicted)
• Water Solubility: Soluble in water.
• BRN: 1726256
• CAS DataBase Reference: (+)-Dimethyl L-tartrate(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Dimethyl L-tartrate(608-68-4)
• EPA Substance Registry System: (+)-Dimethyl L-tartrate(608-68-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 608-68-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(+)-Dimethyl L-tartrate is used as a starting reagent for the synthesis of (+)-Monomorine I, a pyrrolidine-based alkaloid that serves as a trail pheromone for the Pharaoh's ant (Monomorium pharaonis). This application is significant for studying and understanding the chemical communication and behavior of this particular ant species.
Used in Asymmetric Synthesis:
(+)-Dimethyl L-tartrate can react with sulfur tetrafluoride to form dimethyl meso-2,3-difluorosuccinate, which may be used in the synthesis of chiral ligands for asymmetric synthesis. These ligands, such as (2R, 3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol and (-)-(4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane (PYDIPHOS), are crucial in the development of enantioselective catalysts and the production of chiral compounds with high purity and selectivity.
Used in Pharmaceutical Industry:
(+)-Dimethyl L-tartrate is also utilized in the pharmaceutical industry for the synthesis of various chiral drugs and drug intermediates. The ability to produce chiral compounds with high purity and selectivity is essential in the development of new drugs and the improvement of existing ones, as the efficacy and safety of a drug can be significantly influenced by its chirality.

InChI:InChI=1/C6H10O6/c1-11-5(9)3(7)4(8)6(10)12-2/h3-4,7-8H,1-2H3/t3-,4-/m1/s1

Upstream product

• 67-56-1 methanol 
• 87-69-4 L-Tartaric acid 
• 87-91-2 diethyl (2R,3R)-tartrate 
• 87-69-4 tartaric acid 
• 186581-53-3 diazomethane 
• 147-73-9 meso-tartaric acid 
• 622-00-4 dibenzyl (2R,3R)-2,3-dihydroxybutanedioate 
• 624-49-7 dimethylfumarate 
• 149-73-5 trimethyl orthoformate 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 11003-23-9 Elaiophylin 
• 21066-72-8 diethyl tartrate 
• 87-69-4 L-tartaric acid 
• 22335-52-0 dimethyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide 

Downstream Products

• 38270-70-1 dimethyl meso-2,3-O-benzylidenetartrate 
• 909878-64-4 meso-erythritol 
• 6968-16-7 rac-threitol 
• 634-63-9 meso-tartramide 
• 26549-65-5 meso-N,N,N',N',-tetramethyltartaramide 
• 62182-40-5 dimethyl (2R,3S)-2,3-dimethoxysuccinate 
• 117780-08-2 1,1,4,4-tetraphenyl-butane-1,2,3,4-tetraol 
• 67812-37-7 methyl (2R,3R)-2,3-dihydroxy-3-carboxamidopropanoate 
• 634-63-9 (R,R)-tartaric acid diamide 
• 62173-55-1 dimethyl α,α'-dichloro-succinates 
• 38270-72-3 dimethyl 2,3-O-benzylidene-L-tartrate 
• 6304-99-0 dimethyl 2,3-bis(benzoyloxy)succinate 
• 126953-09-1 tartaric acid bis-(N'-phenyl-hydrazide) 

Relevant articles and documents

Synthesis and characterization of monoaryl esters of l-tartaric acid and their process for fries rearrangement

Chiral protected monoaryl esters (2a-2h) were synthesized from monoester of l-tartaric acid, having two asymmetric centers and C2 axis of symmetry. l-tartaric acid was protected and partially hydrolyzed to give the corresponding monoester. Monoester upon treatment with different substituted phenols gave desired monoaryl esters (2a-2h). Fries rearrangement of monoaryl esters was then tried under various conditions by using different Lewis acids. All the compounds were purified and characterized by using spectroscopic techniques like IR, 1H-NMR, 13C-NMR, HRMS-ESI, and elemental analysis. The structure of compound 2e was obtained by X-ray crystallography.

[2]Catenane Synthesis via Covalent Templating

After earlier unsuccessful attempts, this work reports the application of covalent templating for the synthesis of mechanically interlocked molecules (MiMs) bearing no supramolecular recognition sites. Two linear strands were covalently connected in a perpendicular fashion by a central ketal linkage. After subsequent attachment of the first strand to a template via temporary benzylic linkages, the second was linked to the template in a backfolding macrocyclization. The resulting pseudo[1]rotaxane structure was successfully converted to a [2]catenane via a second macrocyclization and cleavage of the ketal and temporary linkages.

Selective Monoacylation of Diols and Asymmetric Desymmetrization of Dialkyl meso-Tartrates Using 2-Pyridyl Esters as Acylating Agents and Metal Carboxylates as Catalysts

With 2-pyridyl benzoates as acylating agents and Zn(OAc)2 as a catalyst, 1,2-diols, 1,3-diols, and catechol were selectively monoacylated. Furthermore, the highly enantioselective desymmetrization of meso-tartrates was achieved for the first time, utilizing 2-pyridyl esters and NiBr2/AgOPiv/Ph-BOX in CH3CN or CuCl2/AgOPiv/Ph-BOX in EtOAc catalyst systems (up to 96% ee). The latter catalyst system was also effective for the kinetic resolution of dibenzyl dl-tartrate.

Practical Cleavage of Acetals by Using an Odorless Thiol Immobilized on Silica

A practical, efficient and general method was developed for the deprotection of a variety of aromatic and aliphatic acetals to their corresponding catechol or diol derivatives using thiol immobilized on silica gel. This is an application for the well-known commercial solid-supported thiol (SiliaMetS Thiol). The procedure is mild and amenable to scale-up. It does not require inert atmosphere and clean conversions were observed. This method is applicable to substituted 1,3-benzodioxole and aliphatic acetals with different functionalities. It offers the advantage of a general route with high yield, which can be undertaken at ambient temperature.

Chiroptical properties of 2,2’-bioxirane

The two enantiomers of 2,2′-bioxirane were synthesized, and their chiroptical properties were thoroughly investigated in various solvents by polarimetry, vibrational circular dichroism (VCD), and Raman optical activity (ROA). Density functional theory (DFT) calculations at the B3LYP/aug-cc-pVTZ level revealed the presence of three conformers (G+, G?, and cis) with Gibbs populations of 51, 44, and 5% for the isolated molecule, respectively. The population ratios of the two main conformers were modified for solvents exhibiting higher dielectric constants (G? form decreases whereas G+ form increases). The behavior of the specific optical rotation values with the different solvents was correctly reproduced by time-dependent DFT calculations using the polarizable continuum model (PCM), except for the benzene for which explicit solvent model should be necessary. Finally, VCD and ROA spectra were perfectly reproduced by the DFT/PCM calculations for the Boltzmann-averaged G+ and G? conformers.

Enantioselective Dihydroxylation of Alkenes Catalyzed by 1,4-Bis(9-O-dihydroquinidinyl)phthalazine-Modified Binaphthyl–Osmium Nanoparticles

A series of unprecedented binaphthyl–osmium nanoparticles (OsNPs) with chiral modifiers were applied in the heterogeneous asymmetric dihydroxylation of alkenes. A remarkable size effect of the OsNPs, depending on the density of the covalent organic shells, on the reactivity and enantioselectivity of the dihydroxylation reaction was revealed. Successful recycling of the OsNPs was also demonstrated and high reaction efficiency and enantioselectivity were maintained.

Based on the chiral diamine spiro skeleton chiral phosphorus nitrile catalyst, preparation method and application thereof

The invention provides a chiral phosphazene catalyst based on a spiro framework adopting chiral diamine, a preparation method and an application of the chiral phosphazene catalyst. The catalyst has a structure represented in the general formula: (RX-)3P=NR', chiral groups are introduced through R and R', and the catalyst has a structure with two seven-membered rings in centered connection through phosphorspirol. Optically pure tartaric acid or substituted hexahydrophthalic acid or 1,2-cyclopentanedicarboxylicacid,(1R,2S)-rel- is taken as a raw material, chiral diamine is generated through esterification, a Grignard reaction, an optional chlorination reaction, an azido reaction and a reduction reaction of the raw material, then chiral diamine and phosphorus pentachloride have a spirocyclization reaction to construct a phosphorspirol-centered screw ring, the chiral phosphazene molecular catalyst is obtained under the alkaline condition, and a method for substituting azido for hydroxyl directly has good application and popularization value. The catalyst has the advantages of high catalysis efficiency, good stereoselectivity, mild conditions, economy, environmental protection, simplicity and convenience in operation and the like as well as popularization and application prospects.

Mechanistically Driven Development of an Iron Catalyst for Selective Syn-Dihydroxylation of Alkenes with Aqueous Hydrogen Peroxide

Product release is the rate-determining step in the arene syn-dihydroxylation reaction taking place at Rieske oxygenase enzymes and is regarded as a difficult problem to be resolved in the design of iron catalysts for olefin syn-dihydroxylation with potential utility in organic synthesis. Toward this end, in this work a novel catalyst bearing a sterically encumbered tetradentate ligand based in the tpa (tpa = tris(2-methylpyridyl)amine) scaffold, [FeII(CF3SO3)2(5-tips3tpa)], 1 has been designed. The steric demand of the ligand was envisioned as a key element to support a high catalytic activity by isolating the metal center, preventing bimolecular decomposition paths and facilitating product release. In synergistic combination with a Lewis acid that helps sequestering the product, 1 provides good to excellent yields of diol products (up to 97% isolated yield), in short reaction times under mild experimental conditions using a slight excess (1.5 equiv) of aqueous hydrogen peroxide, from the oxidation of a broad range of olefins. Predictable site selective syn-dihydroxylation of diolefins is shown. The encumbered nature of the ligand also provides a unique tool that has been used in combination with isotopic analysis to define the nature of the active species and the mechanism of activation of H2O2. Furthermore, 1 is shown to be a competent synthetic tool for preparing O-labeled diols using water as oxygen source.

A quaternary phosphonium salt compound and its preparation method

The present invention discloses a quaternary phosphonium salt compound and a preparation method thereof. The method uses cheap and readily available L-tartaric acid as the raw material, and conducts carboxyl esterification, hydroxyl protection, Grignard reaction, azide substitution, azide reduction and final reaction with phosphorus pentachloride, so as to obtain the quaternary phosphonium salt compound. The quaternary phosphonium salt compound is a novel Bronsted acid catalyst (a hydrogen bond donor catalyst), and can be used in the catalysis of asymmetric Mannich reaction, Michael reaction and Henry reaction.

Synthesis, characterization, antimicrobial and antileishmanial activities of amide derivatives of L-tartaric acid

Sixteen (16) chiral, amides were synthesized from commercially available L-tartaric acid, having two asymmetric centers and C2 axis of symmetry. The diacid functionality of L-tartaric acid was protected as dimethyl ester and dihydroxy groups as acetonoid. The partial hydrolysis of acetonoid of dimethyl ester gave the corresponding monoester. Monoester upon treatment with different substituted aromatic amines gave desired amides (1-8). Amides (1-8) afforded deprotected compounds (9-16) after reacting with acetyl chloride and methanol. All the compounds were characterized by using spectroscopic techniques such as IR, 1H-NMR, 13C-NMR, and EIMS. The compounds gave reasonable elemental analyses. The structure of compound 6 was unambiguously obtained by X-ray crystallography. Protected (1-8) and deprotected amides (9-16) were tested for their antileishmanial (against Leshmania tropica KWH23 Promastigotes) and antimicrobial activities at different concentrations against different strains of bacteria and fungi.