608-40-2

Usage

Uses

Used in Chemical Synthesis:
MESO-2,3-DIMETHYLSUCCINIC ACID is used as a reagent for the synthesis of meso-1,4-diiodo-2,3-dimethylbutane and selenoacetal with an erythro-configured CHMe-CHMe fragment. MESO-2,3-DIMETHYLSUCCINIC ACID is valuable in the preparation of complex organic molecules and has potential applications in various chemical and pharmaceutical industries.
Used in Organic Chemistry Research:
MESO-2,3-DIMETHYLSUCCINIC ACID is also used in the synthesis of other organic compounds, such as erythro-4-acetoxy-2,3-dimethylbutan-1-ol and (±)-faranal. These compounds have potential applications in the fragrance and flavor industries, as well as in the development of new pharmaceutical agents.

Purification Methods

Crystallise the meso-acid from EtOH/ether or EtOH/chloroform.

InChI:InChI=1/C6H10O4/c1-3(5(7)8)4(2)6(9)10/h3-4H,1-2H3,(H,7,8)(H,9,10)/t3-,4+

Upstream product

• 123-91-1 1,4-dioxane 
• 608-40-2 rac-2,3-dimethylsuccinic acid 
• 67-56-1 methanol 
• 2985-33-3 monoethyl methylmalonate 
• 21788-49-8 (E)-2,3-dimethyl-2-butenedioic acid 
• 28895-02-5 3,4-dimethyl-2,5-hexanedione 
• 526-79-4 2,3-dimethyl-4-oxo-valeric acid 
• 802294-64-0 propionic acid 
• 7475-92-5 2,3-dimethylsuccinic anhydride 
• 27697-13-8 2-methyl-3-methylenesuccinic acid 
• 64512-26-1 cis-2,2-dichloro-3,4-dimethylcyclobutanone 
• 149006-66-6 2,3-Dimethyl 2-carboxybutanedioic acid 
• 7664-93-9 sulfuric acid 
• 7722-84-1 dihydrogen peroxide 

Downstream Products

• 608-40-2 rac-2,3-dimethylsuccinic acid 
• 10564-05-3 meso-2.3-dimethyl-succinic acid bis-(4-bromo-phenacyl ester) 
• 766-39-2 2,3-Dimethylmaleic anhydride 
• 16844-07-8 meso-2,3-dimethylsuccinic anhydride 
• 57716-80-0 rac-2,3-dimethylbutane-1,4-diol 
• 74939-90-5 (2R,3S)-2,3-dimethylbutane-1,4-diol 
• 57340-48-4 racem.-2,3-dimethyl-1,4-bis-(toluene-4-sulfonyloxy)-butane 
• 13122-66-2 (+/-)-erythro-4-oxo-2.3-dimethyl-4-phenyl-butyric acid 

Relevant academic research and scientific papers

STEREOSELECTIVE SYNTHESIS OF 3,4-DISUBSTITUTED CYCLOPENTANONES AND RELATED COMPOUNDS

Methods and materials for preparing optically active 3,4-disubstituted cyclopentanones are disclosed. The method includes hydrolyzing one or more compounds represented by Formula (13), or removing an ester moiety from a compound represented by Formula (18).

Double Asymmetric Hydrogenation of Conjugated Dienes Catalysed by Ruthenium-binap Complexes

Buta-1,3-diene-2,3-dicarboxylic acid is smoothly hydrogenated in the presence of ruthenium-(R)-binap complexes as a catalyst via two consecutive 1,2-hydrogen additions, giving rise to (S,S)-2,3-dimethylsuccinic acid with 98percent diastereoisomeric excess and 96percent enantiomeric excess.

Stereoselective homogeneous hydrogenation. The basis of preferential anti-isomer formation in acyclic systems

Directed homogeneous hydrogenation of olefins derived from methyl acrylate proceeds with high selectivity.The reactant must possess a polar substituent at a chiral centre situated in the α'-position; this may be -OH, CO2R or NHCOR.The catalyst should be a cationic chelating rhodium biphosphine complex.In all cases high anti-stereoselectivity is observed in the reduced product, and this can be rationalised by a simple and general model.With an optically active catalyst, efficient kinetic resolution occurs, providing a means of access to optically active acrylates.Experimental details of typical hydrogenation reactions are provided.

HIGHLY DIASTEREOSELECTIVE TANDEM ALKYLATION OF ACYCLIC α,β-UNSATURATED ESTERS BASED ON THE NOVEL USE OF DITHIOACETAL UNIT

Highly diastereoselective tandem alkylation process of acyclic α,β-unsaturated esters was developed based on the novel use of dithioacetal as a stereocontrolling unit.

OXIDATIVE COUPLING REACTIONS UNDER PTC CONDITIONS

Succinic acid derivatives have been prepared from cyanohalides under PTC conditions in good yields.

DIMETALATED TERTIARY SUCCINAMIDES. ALKYLATION AND ANNELATION REACTIONS

The reactions of dimetalated succinamides 1 with a variety of electrophiles give 2,3-disubstituted adducts (2) with high diasterioselectivity and annelated products (6-9).