117384-45-9

Basic information

• Product Name: (+)-DI-TERT-BUTYL L-TARTRATE
• Synonyms: (+)-DI-TERT-BUTYL L-TARTRATE;DI-TERT-BUTYL L-TARTRATE;Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, bis(1,1-diMethylethyl) ester;(R,R)-Di-tert-butyl-tartrat;Di-tert-butyl L-(+)-Tartrate;ditert-butyl (2R,3R)-2,3-dihydroxybutanedioate
• CAS NO: 117384-45-9
• Molecular Formula: C₁₂H₂₂O₆
• Molecular Weight: 262.3
• Product Categories: Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents;EpoxidationChiral Building Blocks;Esters;Organic Building Blocks;Analytical/Chromatography;Ion Sensor Materials;Ionophores Potentiometric for ISE
• Mol File: 117384-45-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 90-92 °C(lit.)
• Boiling Point: 321.8°Cat760mmHg
• Flash Point: 109°(228°F)
• Appearance: White/Solid
• Density: 1.143
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.471
• Storage Temp.: Refrigerator
• Solubility: Acetone (Sparingly), Chloroform (Slightly), Methanol (Slightly)
• PKA: 11.44±0.20(Predicted)
• BRN: 5026723
• CAS DataBase Reference: (+)-DI-TERT-BUTYL L-TARTRATE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-DI-TERT-BUTYL L-TARTRATE(117384-45-9)
• EPA Substance Registry System: (+)-DI-TERT-BUTYL L-TARTRATE(117384-45-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 9-21
• Hazardous Substances Data: 117384-45-9(Hazardous Substances Data)

Usage

General Description

(+)-DI-TERT-BUTYL L-TARTRATE, also known as Di-tert-butyl L-tartrate, is a chiral organic compound with the molecular formula C14H24O6. It is a white crystalline solid that is used as a chiral resolving agent in enantioselective synthesis. (+)-DI-TERT-BUTYL L-TARTRATE is commonly used in the pharmaceutical industry for the separation and analysis of enantiomers, as well as in the production of fine chemicals and specialty materials. It is also an important chiral auxiliary in asymmetric synthesis, and its ability to form inclusion complexes with various organic molecules makes it a versatile compound for use in stereochemistry and asymmetric catalysis. Additionally, it is utilized in the food and beverage industry for its ability to stabilize and enhance the flavor of certain products. The (+)-DI-TERT-BUTYL L-TARTRATE is an important compound with various applications in the fields of chemistry, pharmaceuticals, and food science.

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

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

Downstream Products

• 7633-32-1 tert-butyl glyoxylate 
• 204273-54-1 (2R,3R)-2,3-Bis-[(E)-3-(3,4-diacetoxy-phenyl)-acryloyloxy]-succinic acid di-tert-butyl ester 
• 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 articles and documents

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.

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.

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.