117384-46-0

Usage

Uses

Used in Pharmaceutical Industry:
(-)-DI-TERT-BUTYL D-TARTRATE is used as a resolving agent for the production of optically pure compounds, which is crucial in the development of single-enantiomer drugs. The ability to separate enantiomers ensures that pharmaceuticals can be tailored for specific biological activities, reducing side effects and improving therapeutic outcomes.
Used in Chemical Industry:
In the chemical industry, (-)-DI-TERT-BUTYL D-TARTRATE serves as a chiral auxiliary in organic synthesis, aiding in the creation of enantioselective reactions. This contributes to the synthesis of complex molecules with specific chiral centers, which are essential in the production of specialty chemicals and fine chemicals.
Used in Asymmetric Synthesis:
(-)-DI-TERT-BUTYL D-TARTRATE is utilized as a chiral auxiliary in asymmetric synthesis, enhancing the selectivity of reactions towards the desired enantiomer. This is particularly important in the synthesis of biologically active compounds, where the stereochemistry of a molecule can significantly influence its activity and safety.
Used in Catalysis:
(-)-DI-TERT-BUTYL D-TARTRATE has been investigated for its potential applications in catalysis, where its chiral nature could be employed to create enantioselective catalysts. These catalysts could improve the efficiency and selectivity of chemical reactions, leading to more sustainable and cost-effective processes.
Used in Material Science:
(-)-DI-TERT-BUTYL D-TARTRATE is also being explored for its applications in material science, where its chiral properties could be leveraged to develop new materials with unique optical, electronic, or mechanical properties. This could lead to advancements in various fields, including optoelectronics, sensors, and nanotechnology.

InChI:InChI=1/C12H22O6/c1-11(2,3)17-9(15)7(13)8(14)10(16)18-12(4,5)6/h7-8,13-14H,1-6H3/t7-,8-/m0/s1

Downstream Products

• 193957-75-4 di-tert-butyl (2R,3S)-2-<(1S)-2-(benzyloxy)-1-hydroxyethyl>-1,4-dioxaspiro<4,4>nonane-2,3-dicarboxylate 
• 221693-47-6 di-tert-butyl (2R,3S)-2-<(1R)-2-(benzyloxy)-1-hydroxyethyl>-1,4-dioxaspiro<4,4>nonane-2,3-dicarboxylate 
• 193957-60-7 di-tert-butyl (2R,3S)-4-<(R)-1-hydroxy-1-phenylmethyl>-1,4-dioxaspiro<4.4>nonane-2,3-dicarboxylate 
• 644981-51-1 di-tert-butyl (1S,3R,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-3-[(tert-butyldiphenylsilyl)oxymethyl]-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate 
• 644981-48-6 di-tert-butyl (1S,3R,4S,5R,6R,7R)-7-acetyl-6-benzyloxy-3-[(tert-butyldiphenylsilyl)oxymethyl]-7-hydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate 
• 925453-59-4 di-tert-butyl (1S,3R,4S,5R,6R,7S)-6-benzyloxy-3-[(tert-butyldiphenylsilyl)oxymethyl]-7-hydroxy-7-(1-hydroxyethyl)-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate 
• 644981-50-0 di-tert-butyl (1S,3R,4S,5R,6R,7R)-6-benzyloxy-3-[(tert-butyldiphenylsilyl)oxymethyl]-7-hydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate 
• 644981-49-7 di-tert-butyl (1S,3R,4S,5R,6S)-6-benzyloxy-3-[(tert-butyldiphenylsilyl)oxymethyl]-1-[2-(methoxymethoxy)ethyl]-7-oxo-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate 
• 644981-47-5 di-tert-butyl (1S,3R,4S,5R,6R,7R)-7-acetyl-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate 
• 644981-46-4 di-tert-butyl (1S,3R,4S,5R)-7-acetyl-3-[(tert-butyldiphenylsilyl)oxymethyl]-1-[2(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]oct-6-ene-4,5-dicarboxylate 
• 644981-53-3 tri-tert-butyl (1S,3S,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-1-[2-(methoxymethoxy)ethyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate 
• 925453-61-8 tri-tert-butyl (1S,3S,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-1-(2-hydroxyethyl)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate 

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.

Aldol reactions of ketal-protected tartrate ester enolates. Asymmetric syntheses and absolute stereochemical assignments of phospholipase A2 inhibitors cinatrin C1 and C3

An efficient approach to the syntheses of cinatrins C1 and C3 has been developed and used to establish the absolute configurations of these natural products. The construction of each molecule has been achieved in a five-step reaction sequence (overall yield 43% for cinatrin C1, 33% for cinatrin C3) from the di-tert-butyl ester of (R,R)-tartaric acid. The two contiguous, quaternary chiral centers in the cinatrin skeleton are constructed via a diastereoselective, titanium-mediated aldol coupling of a tartrate-derived silylketene acetal and an achiral α-ketoester. This bond construction proceeds with excellent diastereoselectivity for a variety of aldehyde and α-ketoester substrates.