22644-27-5

Usage

Uses

Used in Pharmaceutical Industry:
Dimethyl (R)-(+)-methylsuccinate is used as a key intermediate in the synthesis of FK-506, a potent immunosuppressive macrolide antibiotic. Dimethyl (R)-(+)-methylsuccinate is particularly effective in preventing organ transplant rejection and treating autoimmune diseases due to its ability to inhibit the activation of T cells.
Additionally, its chiral nature makes it a valuable building block for the development of other enantiomerically pure pharmaceuticals, which can have improved efficacy and reduced side effects compared to their racemic counterparts.
Used in Chemical Synthesis:
Dimethyl (R)-(+)-methylsuccinate is also used as a versatile building block in the synthesis of various chiral compounds for different applications in the chemical industry. Its unique structure allows for the creation of a wide range of products, including specialty chemicals, fragrances, and agrochemicals, with potential benefits in terms of selectivity and reduced environmental impact.

InChI:InChI=1/C7H12O4/c1-5(7(9)11-3)4-6(8)10-2/h5H,4H2,1-3H3/t5-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 3641-51-8 2-(R)-methylsuccinic acid 
• 21307-96-0 methyl 2-methylsuccinate 
• 617-52-7 Dimethyl itakonate 
• 617-54-9 citraconic acid dimethyl ester 
• 617-53-8 mesaconic acid dimethyl ester 
• 1333-74-0 hydrogen 
• 1283688-50-5 methyl (3R)-4,4,4-trimethoxy-3-methylbutanoate 
• 3377-21-7 dimethyl 2-methylenemalonate 
• 67-56-1 methanol 
• 498-21-5 2-methylbutanedioic acid 
• 73964-90-6 5-methyl-(3H,5H)-tetrahydrothiophene-2,4-dione 
• 617-86-7 triethylsilane 
• 75-36-5 acetyl chloride 

Downstream Products

• 83509-04-0 (R)-2-methylsuccinate-1-monomethyl ester 
• 23268-03-3 (R)-2-methyl-succinic acid 4-methyl ester 
• 83084-78-0 (R)-4-(4-Benzyl-5-oxo-2-phenyl-4,5-dihydro-oxazol-4-yl)-2-methyl-4-oxo-butyric acid methyl ester 
• 2938-98-9 (R)-2-methylbutane-1,4-diol 
• 120329-64-8 (R)-2-methylbutane-1,4-diol dibenzoate 
• 281214-26-4 (R)-2-methylbutane-1,4-diyl bis(4-methylbenzenesulfonate) 
• 82291-89-2 (R)-5-Benzoylamino-2-methyl-4-oxo-6-phenyl-hexanoic acid 
• 83084-79-1 (R)-5-Benzoylamino-2-methyl-4-oxo-6-phenyl-hexanoic acid methyl ester 
• 83148-63-4 (S)-1-((2R,5R)-5-Benzoylamino-2-methyl-4-oxo-6-phenyl-hexanoyl)-pyrrolidine-2-carboxylic acid 
• 83148-65-6 (S)-1-((2R,5S)-5-Benzoylamino-2-methyl-4-oxo-6-phenyl-hexanoyl)-pyrrolidine-2-carboxylic acid 
• 83084-81-5 5-benzamido-2-methyl-4-oxo-6-phenylhexanoyl-L-proline 
• 83084-81-5 5-benzamido-2(R)-methyl-4-oxo-6-phenylhexanoyl-L-proline 
• 498-23-7 citraconic acid 
• 71028-76-7 2-methyl-but-2-enedioic acid 1-methyl ester 

Relevant academic research and scientific papers

The use of new carboranylphosphite ligands in the asymmetric Rh-catalyzed hydrogenation

A series of new monodentate phosphite ligands based on carboranes have been synthesized and used for asymmetric Rh-catalyzed hydrogenation of prochiral olefins in CH2Cl2 with the result of up to 99.5% ee. High reactivities (100% conv

Me-AnilaPhos: a new chiral phosphine-phosphoramidite ligand for a highly efficient Rh-catalyzed asymmetric olefin hydrogenation

A cationic rhodium(I) complex with a novel chiral phosphine-phosphoramidite ligand based on 2-diphenylphosphino-N-methylaniline and R-BINOL moieties has been synthesized. The complex provided remarkably high activity and enantioselectivity in the asymmetr

Chiral carborane-derived thiophosphites: A new generation of ligands for Rh-catalyzed asymmetric hydrogenation

A new class of chiral monodentate ligands - carborane-containing thiophosphites have been synthesized and tested in the Rh-catalyzed asymmetric hydrogenation of prochiral olefins with the result of up to 99% ee. The dependence of the enantioselectivity on

New ionic phosphite ligands: Synthesis and application in asymmetric Rh-catalyzed hydrogenation

A series of chiral ionic phosphite-type ligands bearing pyridinium and imidazolium fragments were prepared. Testing of these ligands in Rh-catalyzed asymmetric hydrogenation of dimethyl itaconate and methyl 2-acetamidoacrylate resulted in 95% ee of the products with 100% conversion of the reactants.

Phosphorodiamidite derivatives of 1,1'-bi-2-naphthol containing stereogenic phosphorus atoms as ligands in enantioselective catalysis

P*-Mono- and P*,P*-bidentate phosphorodiamidites containing the (Sa)-1,1'-binaphthyl core and 1,3,2-diazaphospholidine rings were synthesized. The use of these compounds in the rhodium-catalyzed asymmetric hydrogenation, as well as in the palla

BINOL-derived diphosphoramidites bearing unsymmetrical 1,2-diamine link and their application in asymmetric catalysis

New P,P-bidentate diastereomeric diphosphoramidite chiral ligands with mixed stereogenic elements and a C1 backbone symmetry have been prepared from (Sa)- and (Ra)-1,1′-binaphthyl-2, 2′-diol (BINOL) and (S)-N-benzyl-1-(pyr

Chiral supported ionic liquid phase (CSILP) catalysts for greener asymmetric hydrogenation processes

Chiral supported ionic liquid phase (CSILP) catalysts were prepared by physical adsorption (within highly porous carbons or mesoporous silica) of Ir, Ru and Rh complexes as IrCl(COD)-(S,S)-BDPP, [IrCl-(S)-BINAP]2, RuCl(p-cymene)[(S,S)-Ts-DPEN],

Using Data Science To Guide Aryl Bromide Substrate Scope Analysis in a Ni/Photoredox-Catalyzed Cross-Coupling with Acetals as Alcohol-Derived Radical Sources

Ni/photoredox catalysis has emerged as a powerful platform for C(sp2)–C(sp3) bond formation. While many of these methods typically employ aryl bromides as the C(sp2) coupling partner, a variety of aliphatic radical sources have been investigated. In principle, these reactions enable access to the same product scaffolds, but it can be hard to discern which method to employ because nonstandardized sets of aryl bromides are used in scope evaluation. Herein, we report a Ni/photoredox-catalyzed (deutero)methylation and alkylation of aryl halides where benzaldehyde di(alkyl) acetals serve as alcohol-derived radical sources. Reaction development, mechanistic studies, and late-stage derivatization of a biologically relevant aryl chloride, fenofibrate, are presented. Then, we describe the integration of data science techniques, including DFT featurization, dimensionality reduction, and hierarchical clustering, to delineate a diverse and succinct collection of aryl bromides that is representative of the chemical space of the substrate class. By superimposing scope examples from published Ni/photoredox methods on this same chemical space, we identify areas of sparse coverage and high versus low average yields, enabling comparisons between prior art and this new method. Additionally, we demonstrate that the systematically selected scope of aryl bromides can be used to quantify population-wide reactivity trends and reveal sources of possible functional group incompatibility with supervised machine learning.

Chiral phosphine-phosphoramidite ester ligand as well as preparation method and application thereof

The invention provides a method for preparing a phosphine-phosphoramidite ester ligand from a chiral beta-aminophosphine intermediate and an application of the phosphine-phosphoramidite ester ligand in an asymmetric reaction. Chiral N-(2-(phosphoryl)-1-phenethyl) amide is prepared from the chiral beta-aminophosphine intermediate through an asymmetric hydrogenation reaction of (Z)-(alpha-aryl-beta-phosphoryl) alkenyl amide, and then hydrolysis reduction. The preparation method comprises the following steps: dissolving newly-prepared chlorinated phosphite in toluene, adding a solution formed by dissolving the chiral phosphine-amine compound and triethylamine in toluene into an ice-water bath according to a molar ratio of the chiral phosphine-amine compound to the chlorinated phosphite to the triethylamine of 1: (1-2): (3-5), heating the reaction solution to 18-25 DEG C, stirring and reacting for 10-30 hours, filtering, and carrying out column chromatography to remove the solvent, and recrystallizing to obtain the required phosphine-phosphoramidite ligand. According to the present invention, the asymmetric hydrogenation reaction of the catalyst formed by the ligand and the metal precursor on the double bonds such as C = C, C = N, C = O and the like can achieve the enantioselectivity of 99%; the catalyst is high in activity, and TON reaches up to 10000.

Chiral ferrocene phosphine-indole aminophosphine ligand as well as preparation method and application thereof

The invention discloses a chiral ferrocene phosphine-indole aminophosphine ligand as well as a preparation method and application thereof. The preparation method comprises the following steps: dissolving a chiral ferrocene phosphine-indole intermediate in