110556-33-7

Usage

Uses

Used in Pharmaceutical Synthesis:
METHYL (R)-(+)-3-BROMO-2-METHYLPROPIONATE is used as a reactant for the preparation of (S)-3-(6-Methoxy-pyridin-3-yl)-2-methylpropionic acid methylester, which is an important intermediate in the synthesis of decahydroisoquinoline derivatives, such as NVP-ACQ090. NVP-ACQ090 is a potent antagonist of the somatostatin sst3 receptor, playing a crucial role in the treatment of neurological disorders.
Used in Enantioselective Reactions:
METHYL (R)-(+)-3-BROMO-2-METHYLPROPIONATE is used as a reference compound in the enantioselective alkylation reaction of hydrophobic vitamin B12 derivatives. This application is essential for the development of novel chiral catalysts and the synthesis of enantiomerically pure compounds with potential pharmaceutical applications.

InChI:InChI=1/C5H9BrO2/c1-4(3-6)5(7)8-2/h4H,3H2,1-2H3/t4-/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 110595-22-7 (R)-4-acetoxy-3-methyl-1-butene 
• 80657-57-4 3-hydroxy-(2S)-methylpropionate 
• 72657-23-9 methyl (R)-3-hydroxy-2-methylpropionate 
• 20609-71-6 3-bromo-2-methyl-propionic acid methyl ester 
• 142402-78-6 methyl (2S)-3-hydroxy-2-methyl-3-(methylsulfonyloxy)propanoate 
• 73295-10-0 (S)-3-acetoxy-2-methyl-propionic acid methyl ester 

Downstream Products

• 38574-62-8 methyl (S)-(+)-2-benzylpropionate 
• 123154-31-4 (R)-2-methoxycarbonylpropyltriphenylphosphonium bromide 
• 1353161-22-4 methyl N-benzyl-2-(2-methoxycarbonyl-(S)-2-methylethyl)azetidine-2-carboxylate 
• 126522-30-3 (S)-3-(3-methoxycarbonylbutyl)-1-tosylindole 
• 123154-32-5 (Z),(S)-3-(3-methoxycarbonyl-1-butenyl)-1-tosylindole 

Relevant academic research and scientific papers

Efficient procedures to prepare primary and secondary alkyl halides from alkanols via the corresponding sulfonates under mild conditions

The study presented herein shows that sulfonate/halide exchange can be advantageously performed in THF to avoid several side reactions such as elimination and epimerization when the reaction is performed from a chiral alkyl sulfonate or a substrate having a C-H acidic chiral center. The main limitation of this procedure was found to be the conversion of secondary alkyl sulfonates to alkyl chlorides. In this case, the addition of a catalytic amount of manganese chloride clearly accelerates the rate and the efficiency of the reaction. Copyright

Enantioselectivity of haloalkane dehalogenases and its modulation by surface loop engineering

In the loop: Engineering of the surface loop in haloalkane dehalogenases affects their enantiodiscrimination behavior. The temperature dependence of the enantioselectivity (lnE versus 1/T) of β-bromoalkanes by haloalkane dehalogenases is reversed (red data points) by deletion of the surface loop; the selectivity switches back when an additional single-point mutation is made. This behavior is not observed for -bromoesters.

Asymmetric synthesis of 2-alkyl-3-phosphonopropanoic acids via P - C bond formation and hydrogenation

Allylic acetates, formed by the acetylation of Baylis Hillman adducts, undergo addition of phosphorus nucleophiles to give stereoselectively the Z-unsaturated esters. TFA cleavage of the fert-butyl ester and asymmetric hydrogenation of the unsaturated aci

Diastereoselective palladium(O)-catalyzed azidation of 1- alkenylcyclopropyl esters: Asymmetric synthesis of (-)-(1R,2S)-norcoronamic acid

Palladium(0)-catalyzed azidation of (1R,2S)-l-(1-alkenyl)2- methylcyclopropyl esters 10a,b proceeds with complete retention of configuration to provide, after reduction of the azide and oxidative cleavage of the allylic double bond, the (1R,2S)-norcoronam

SYNTHESIS OF THE (S)-ENANTIOMER OF PANICULIDINE A. ABSOLUTE CONFIGURATION OF NATURAL PANICULIDINES

The (S)-enantiomer of paniculidine A (an indole alkaloid from the plant Murraya paniculata) was synthesized from (R)-5-acetoxy-4-methylpentanoic acid by its oxidative transformation into (S)-methyl 2-methyl-3-acetoxypropionate, substitution of the acetoxy group by bromine, Wittig reaction of (R)-2-methoxycarbonylpropyltriphenylphosphonium bromide with 1-tosyl-3-formylindole, hydrogenation of the side chain of (Z,S)-3-(3-methoxycarbonyl-1-butenyl)-tosylindole and reductive desulfonylation of (S)-3-(3-methoxycarbonylbutyl)-1-tosylindole.Comparison of the D values of the synthesized (S)-paniculidine A with published data for the natural product showed that the latter has the (R) configuration.Condensation of the (R)-4-(2-tetrahydropyranyloxy)-3-methylbromobutane obtained from (R)-5-acetoxy-4-methylpentanoic acid with β-indolylmagnesium iodide followed by removal of the tetrahydropyranyl protecting group gave the (R)-enantiomer of paniculidinol .Its (S)-enantiomer was prepared by hydride reduction of (S)-paniculidine A.

Synthesis of the S-Enantiomer of Paniculidine A: Absolute R-Configuration of the Natural Paniculidines A and B

The absolute R-configuration of both the title monochiral indole alkaloids has been established.

CHIRAL ZINC HOMOENOLATE OF METHYL ISOBUTYRATE. A NEW BUILDING BLOCK FOR THE SYNTHESIS OF CHIRAL α-METHYLESTERS

Chiral homoenolate of methyl isobutyrate prepared in a few steps from optically active methyl β-hydroxy isobutyrate reacts with carbon electrophiles to give chiral α-methyl esters.