622-00-4

Usage

Uses

Used in Organic Synthesis:
L-Tartaric acid dibenzyl ester is used as a reagent in organic synthesis for its ability to facilitate the asymmetric synthesis of organic compounds, enhancing the production of specific enantiomers in chemical reactions.
Used as a Chiral Auxiliary in Pharmaceutical Synthesis:
In the pharmaceutical industry, L-Tartaric acid dibenzyl ester is used as a chiral auxiliary to control the stereochemistry of reactions, ensuring the production of desired enantiomers in the synthesis of pharmaceuticals and other organic compounds. This application is crucial for the development of effective and safe medications.

InChI:InChI=1/C18H18O6/c19-15(17(21)23-11-13-7-3-1-4-8-13)16(20)18(22)24-12-14-9-5-2-6-10-14/h1-10,15-16,19-20H,11-12H2/t15-,16-/m1/s1

Upstream product

• 87-69-4 L-Tartaric acid 
• 100-51-6 benzyl alcohol 
• 52709-42-9 benzylglyoxylate 
• 100-39-0 benzyl bromide 
• 643028-20-0 dibenzyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide 
• 97-72-3 2-Methylpropionic anhydride 
• 5005-35-6 2-pyridyl benzoate 
• 622-00-4 dibenzyl (+)-tartrate 

Downstream Products

• 52709-42-9 benzylglyoxylate 
• 608-68-4 dimethyl L-tartrate 
• 130678-34-1 Dibenzyl-(4R,5R)-2-<(RS)-4,8-dimethylnonyl>-2-methyl-1,3-dioxolan-4,5-dicarboxylat 
• 103710-70-9 Dibenzyl (2R,3R)-2-O-Benzyltartrate 
• 128971-82-4 (4R,5R)-Dibenzyl 1,3,2-Dioxathiolane-4,5-dicarboxylate 2,2-Dioxide 
• 119197-63-6 (R,R)-O-tert-butyl-dibenzyl tartrate 
• 119197-64-7 (R,R)-O,O-di-tert-butyl-dibenzyl tartrate 
• 158732-36-6 benzyl (2R,3R)-3-hydroxy-2-<(2,6-dimethoxybenzoyl)-oxy>butanedioate 
• 158732-35-5 (R,R)-1,2-bis(benzyloxycarbonyl)-2-hydroxyethyl benzoate 
• 488148-82-9 dibenzyl (-)-(2R,3R)-2,3-bis{3-[2,3-bis(3,4-dibenzyloxy)phenyl]prop-2-enoyloxy}-L-tartrate 
• 441024-69-7 dibenzyl (2R,3R)-2,3-bis(hexadecanoyloxy)butanedioate 
• 643028-20-0 dibenzyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide 
• 1448779-05-2 C₂₇H₂₄O₉ 
• 1448779-09-6 C₃₁H₃₄O₇ 

Relevant academic research and scientific papers

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.

New pH-responsive gemini lipid derived co-liposomes for efficacious doxorubicin delivery to drug resistant cancer cells

A gemini version of the amphiphile palmitoyl homocysteine was synthesized. Co-liposomes were prepared using the gemini along with a natural zwitterionic lipid, DOPE and cholesterol at specified ratios. This afforded pH-responsive co-liposomes which could efficiently transport the anticancer drug, doxorubicin (DOX), across the DOX-resistant HeLa cancer cells in response to low pH of cellular endosomes.

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts

An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).

The catalytic synthesis of carboniolamide: The role of sp 3 hybridized oxygen

A catalytic synthesis of carboniolamide has been reported. The strategy was straightforward with aldehyde and amide as starting materials. The products can be isolated as precipitates from the reaction mixture. The factor that stabilizes the labile functionality of hemiaminal was elucidated as a sp 3 hybridized oxygen.

The catalytic synthesis of carboniolamide: The role of sp 3 hybridized oxygen

A catalytic synthesis of carboniolamide has been reported. The strategy was straightforward with aldehyde and amide as starting materials. The products can be isolated as precipitates from the reaction mixture. The factor that stabilizes the labile functionality of hemiaminal was elucidated as a sp 3 hybridized oxygen.

The discovery of a facile access to the synthesis of NSAID dendritic prodrugs

An efficient and straightforward method for the preparation of dendritic prodrugs is reported. Based on this new approach, a class of biodegradable dendrimers has been synthesised from L-tartaric acid and one of the nonsteroidal anti-inflammatory drugs, namely, aspirin or ibuprofen Tianjin Key Laboratory for Modern Drug Delivery and High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin Universit ,Tianjin 300072, P. R. China.

SATURATED FUSED [1,2-B] PYRIDAZINONE COMPOUNDS

The invention is directed to saturated fused [1,2-b]pyridazinone compounds and pharmaceutical compositions containing such compounds that are useful in treating infections by hepatitis C virus.

2-Chloro-(4R,5R)-bis[(1R,2S,5R)-menth-1-yloxycarbonyl]-1,3, 2-dioxaphospholane: A practical chiral pool-derived reagent for determining enantiomeric purity of alcohols

(Chemical Equation Presented) 2-Chloro-(4R,5R)-bis[(1R,2S,5R)-menth-1- yloxycarbonyl)]-1,3,2-dioxaphospholane is a practical reagent for reliably determining enantiomeric purity of chiral alcohols via 31P NMR spectroscopy. The compound is available as a crystalline solid on a 20 g scale from PCl3 and bis[(1R,2S,5R)-menth-1-yl] tartrate. It is comparatively inert toward spontaneous hydrolysis under conventional laboratory conditions but undergoes quantitative substitution of alkoxide for chloride if treated with a chiral alcohol. Nonequivalent 31P NMR signals of diastereomeric 2-alkoxy-1,3,2-dioxophospholanes were dispersed by ～1.4-0.1 ppm. The associated integral ratios reflected enantiomeric purities of preweighted samples of (R)- and (S)-1-phenylethanol, (+)- and (-)-menthol, and a set of primary, secondary, and tertiary alcohols with a precision of ±0.4-1.0%.

Synthesis and chiroptical properties of a new type of chiral depsipeptide dendrons

A new type of chiral depsipeptide dendrons based on tartaric acid as branching juncture and ω-aminocapronic acid as spacer has been prepared. Natural and unnatural tartaric acid building blocks have been incorporated, providing access to combinatorial libraries. All compounds have been completely characterized by FAB-MS, EA analysis, 1H/13C NMR- and UV/Vis-spectroscopy. 1H NMR relaxation measurements have been used to examine the conformational flexibility of these dendrons in CH3CN and CH3OH and indicate a less flexible structure in CH3CN. Pulse gradient spin echo (PGSE) NMR measurements correlate these findings to molecular dimensions. A reduced size for the dendrons in CH3CN compared to CH3OH leads to the assumption of a more compact structure in this solvent. Additional polarimetric data reveal, that observed changes in optical activity with increasing generation can in CH3OH be explained by constitutional effects of the dendron structure but not in CH3CN. CD measurements are in agreement with these findings and show a linear increase of the Cotton effects with increasing generation for CH3OH but not for CH3CN. It can be concluded that the conformation within the dendrons is very sensitive to environmental conditions and that a chiral secondary structure might be stabilized in CH3CN. Initial studies revealed that chirality transfer to the focal functionality occurs.

An improved synthesis of aziridine-2,3-dicarboxylates via azido alcohols - Epimerization studies

The reasons for epimerization of 3-azido-2-hydroxysuccinates observed during the ring opening of epoxides or cyclic sulfites with sodium azide is now clarified. It is caused by the high acidity of the proton at the 3-position. This is proven by a proton deuterium exchange in assays with either D 2O or DCl containing solvents. The anti-3-azido-2-hydroxysuccinates serve as intermediates for enantiomerically pure trans-aziridine-2,3- dicarboxylates for which an optimized synthetic pathway is presented. The first example of an enantiomerically pure mixed diester of the aziridine-2,3- dicarboxylic acid the synthesis of the allyl ethyl ester is reported herein.