117384-45-9

Usage

Uses

Used in Pharmaceutical Industry:
(+)-DI-TERT-BUTYL L-TARTRATE is used as a chiral resolving agent for the separation and analysis of enantiomers. Its application is crucial in ensuring the purity and effectiveness of pharmaceutical compounds, as different enantiomers can have distinct biological activities and effects.
Used in Production of Fine Chemicals and Specialty Materials:
(+)-DI-TERT-BUTYL L-TARTRATE is utilized as an important chiral auxiliary in asymmetric synthesis. Its ability to form inclusion complexes with various organic molecules makes it a versatile compound for use in stereochemistry and asymmetric catalysis, which are essential for the production of high-quality fine chemicals and specialty materials.
Used in Food and Beverage Industry:
(+)-DI-TERT-BUTYL L-TARTRATE is used as a stabilizer and flavor enhancer in the food and beverage industry. Its capacity to stabilize certain products and enhance their flavors contributes to the overall quality and consumer appeal of these products.

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-/m1/s1

Upstream product

• 117384-47-1 O,O′-diacetyl di-tert-butyl L-tartrate 
• 87-69-4 L-Tartaric acid 
• 75-65-0 tert-butyl alcohol 
• 51591-38-9 O,O′-diacetyl L-tartaric acid 

Downstream Products

• 204273-54-1 (2R,3R)-2,3-Bis-[(E)-3-(3,4-diacetoxy-phenyl)-acryloyloxy]-succinic acid di-tert-butyl ester 
• 7633-32-1 tert-butyl glyoxylate 
• 1134634-63-1 di-tert-butyl (2R,3R)-2-hydroxy-3-{[5-oxido-4-(phenylsulphonyl)-1,2,5-oxadiazol-3-yl]-oxy}-succinate 
• 488760-74-3 tert-butyl (4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-(E)-2-hexenoate 
• 488760-73-2 tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-6-phenyl-(E)-2-hexenoate 
• 160803-09-8 tert-butyl (4S,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-(E)-2-hexenoate 

Relevant academic research and scientific papers

Novel fullerene derivatives as dual inhibitors of Hepatitis C virus NS5B polymerase and NS3/4A protease

We evaluated the Hepatitis C virus (HCV) NS5B polymerase and HCV NS3/4A protease inhibition activities of a new set of proline-type fullerene derivatives. All of the compounds had the potential to inhibit both the enzymes, indicating that the fullerene derivatives may be dual inhibitors against NS5B and NS3/4A and could be novel lead compounds for the treatment of HCV infections.

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.

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.

Diastereoselective reduction of a chiral N-Boc-protected δ-amino-α,β-unsaturated γ-keto ester Phe-Gly dipeptidomimetic

The readily available N-Boc-protected δ-amino α,β-unsaturated γ-keto ester 1 was diastereoselectively reduced to the corresponding alcohols 2 and 3, using boron- and aluminum-based reducing reagents. Reduction reactions were successful and resulted in anti/syn ratios of alcohols of >95:5 (80% yield), using LiAlH(O-t-Bu)3 in EtOH at -78 °C under chelation control, and 5:95 (98% yield), using NB-Enantride in THF at -78 °C under Felkin-Anh control.

tert-BUTYL ESTERS AND ETHERS OF (R,R)-TARTARIC ACID

The unknown tert-butyl esters 2a,b and -ethers 4a,b of otherwise nonsubstituted optical pure (R,R)-tartaric acid are synthesized.Esters are made by reaction of O,O-diacyl protected tartaric acid with isobutene and selective cleavage via transesterification of the protective groups.Ethers are formed by reaction of dibenzyl tartrate with isobutene followed by hydrogenolysis of the benzyl groups.Saponification of the corresponding dimethyl tartrate led to partial racemization forming up to 50percent meso product.