83509-04-0

Basic information

• Product Name: Butanedioic acid, methyl-, 1-methyl ester, (R)-
• CAS NO: 83509-04-0
• Molecular Formula: C6H10O4
• Molecular Weight: 146.143
• Mol File: 83509-04-0.mol

Chemical Properties

• CAS DataBase Reference: Butanedioic acid, methyl-, 1-methyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanedioic acid, methyl-, 1-methyl ester, (R)-(83509-04-0)
• EPA Substance Registry System: Butanedioic acid, methyl-, 1-methyl ester, (R)-(83509-04-0)

Safety Data

• Hazardous Substances Data: 83509-04-0(Hazardous Substances Data)

Upstream product

• 71-23-8 propan-1-ol 
• 21307-96-0 methyl 2-methylsuccinate 
• 22644-27-5 (R)-methylsuccinic acid dimethyl ester 
• 3377-31-9 methyl itaconate 
• 67-56-1 methanol 
• 4100-80-5 2-methylsuccinic anhydride 
• 617-54-9 citraconic acid dimethyl ester 

Downstream Products

• 4454-18-6 (R,R)-2,5-dimethyl-adipic acid 
• 19550-58-4 (S,S)-2,5-dimethyl-adipic acid dimethyl ester 

Relevant articles and documents

A three-enzyme system involving an ene-reductase for generating valuable chiral building blocks

The use of ene-reductase (ERED) enzymes for the asymmetric reduction of olefins offers a green, renewable alternative to metal-catalysed asymmetric reduction. We report herein the first example of an ERED-catalysed enantiospecific reduction carried out at large scale using a carbonyl reductase (CRED) enzyme in the cofactor recycle. This reaction has been paired with a hydrolase-mediated regioselective ester hydrolysis to generate a valuable chiral building block using a straightforward one-pot process. Copyright

Expanding the scope of atropisomeric monodentate P-donor ligands in asymmetric catalysis: Hydrogen-transfer reduction of α,β-unsaturated acid derivatives by rhodium/Ph-binepine catalysts

A range of α,β-unsaturated acids and esters have been selectively reduced to the corresponding saturated acid derivatives by hydrogen transfer. As the reducing agent, formic acid was used in the presence of Rh 1 complexes formed with the powerful chiral ligand Ph-binepine (1), an axially chiral binaphthalene-type monodentate P-donor ligand. Very high stereoselectivities (up to 97% ee) were obtained in the case of itaconic acid (2a).

NOVEL BISPHOSPHANE CATALYSTS

In the present Application protection is sought for compounds of the general formula (I) as ligands for reactions catalysed by transition metals. The preparation thereof and use thereof, in particular for the preparation of β-amino acids, is also discusse

Highly enantioselective rhodium-catalyzed hydrogenation of 2-(2-methoxy-2-oxoethyl)acrylic acid - A convenient access of enantiomerically pure isoprenoid building blocks

Asymmetric catalytic hydrogenation of 2-(2-methoxy-2-oxoethyl)acrylic acid (5) to give (2S)-4-methoxy-2-methyl-4-oxobutanoic acid [(S)-6] was studied. An enantiomeric excess of 99.7% ee was achieved with a catalyst formed in situ from [Rh(COD)2]BF4 and the chiral phosphite L2 in 1,2-dichloroethane as solvent. In addition, enzyme-catalyzed semi-saponification of dimethyl 2-methylsuccinate was investigated. Mono ester (S)-6 was transformed into a few compounds which can serve as C 5-building blocks in natural product syntheses. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Hybrid P-chiral diphosphines for asymmetric hydrogenation

A family of diphosphine ligands has been prepared by Michael addition of o-anisylphenyl phosphide to diethyl vinylphosphonate and elaboration to phospholanes based on hexane-2,5-diol or mannitol; some preliminary results of Rh-complex catalysed hydrogenations are reported.

Asymmetric Hydrogenation of Prochiral Alkenes Catalysed by Ruthenium Complexes of (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

Two chiral ruthenium(II) complexes containing (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl were found to be effective catalysts for the asymmetric hydrogenation of 2-acylaminoacrylic and 2-acylaminocinnamic acids under mild conditions, to afford N-acyl-(R)-α-amino acids with 49 - 95 percent optical purity.The differences between the asymmetric hydrogenations effected by RuII- and RhI-(R)-BINAP systems are discussed.Asymmetric hydrogenation of methylenesuccinic acid and its derivatives with Ru-(R)-BINAP is also described.

RUTHENIUM(II)-BINAP COMPLEX CATALYZED ASYMMETRIC HYDROGENATION OF UNSATURATED DICARBOXYLIC ACIDS

Asymmetric hydrogenation of unsaturated dicarboxylic acids employing ruthenium-BINAP complexes as catalyst gave optically active 2-alkylsuccinic acids with high enantioselectivities.

Selectivity in the transesterification of esters by supported enzymes

The regio and enantioselectivities of the transesterification of racemic dimethyl esters by supported enzymes in absence of solvent are studied: preparations of chiral succinates and N-acetyl aminoesters are reported.

Derivatives of the potent angiotensin converting enzyme inhibotor 5(S)-benzamido-4-oxo-6-phenylhexanoyl-L-proline: Effect of changes at positions 2 and 5 of the hexanoic acid portion

Several derivatives of the potent angiotensin converting enzyme inhibitor 5(S)-benzamido-4-oxo-6-phenylhexanoyl-L-proline (1) were synthesized and tested for converting enzyme inhibition activity and blood pressure lowering effects in rats. One compound, 5(S)-benzamido-2(R)-methyl-4-oxo-6-phenylhexanoyl-L-proline (2a), had an I50 against angiotensin converting enzyme of 1.0 x 10-9 M and is the most potent inhibitor prepared thus far in this class of compounds. Testing of 2a orally at 30 mg/kg for inhibition of the angiotensin I induced blood pressure increase in conscious normotensive rats gave 100% inhibition that required 143 min before the angiotensin I blood pressure response returned to 70% of the pretreatment control response. In the conscious renal hypertensive rat, 2a given orally at a dose of 3 mg/kg caused a lowering of blood pressure that reached its maximum of 40 mmHg 8 h following drug administration.