63696-99-1

Usage

Uses

Used in Pharmaceutical Industry:
L(-)-METHANESULFONYLETHYLLACTATE is used as a reactant for the asymmetric synthesis of bioactive compounds, specifically 8,4''-oxyneolignans such as virolin, surinamensin, and their analogs. These compounds exhibit anti-protozoal activity, making them valuable in the development of treatments for various parasitic diseases.

Upstream product

• 687-47-8 (S)-Ethyl lactate 
• 124-63-0 methanesulfonyl chloride 
• 97-64-3 ethyl L-lactate 
• 97-64-3 ethyl 2-hydroxypropionate 
• 7699-00-5 (R)-Ethyl lactate 

Downstream Products

• 72959-94-5 (R)-(+)-ethyl 2-fluoropropionate 
• 117819-33-7 (R)-(+) ethyl 2-(3-benzoylphenoxy)propionate 
• 84049-31-0 (2R,4S)-3-aza-2-methyl-4-phenyl-ethylpentanoate 
• 87726-81-6 (2S,4S)-3-aza-2-methyl-4-phenyl-ethylpentanoate 
• 76671-56-2 (R)-2-phenoxypropionic acid ethyl ester 
• 94202-83-2 ethyl (R)-2-(phenylselenyl)propionate 
• 152981-72-1 (R)-2-(2,6-Dimethyl-phenoxy)-propionic acid ethyl ester 
• 152981-67-4 (R)-2-m-Tolyloxy-propionic acid ethyl ester 
• 153546-15-7 (R)-2-p-Tolyloxy-propionic acid ethyl ester 
• 153546-20-4 (R)-2-(4-Benzoyl-phenoxy)-propionic acid ethyl ester 
• 135425-16-0 (R)-2-{2-[(3-Trifluoromethyl-phenylamino)-methyl]-piperidin-1-yl}-propionic acid ethyl ester 
• 109423-87-2 (R)-2-(3-Chloro-phenoxy)-propionic acid ethyl ester 
• 152981-65-2 (R)-2-o-Tolyloxy-propionic acid ethyl ester 
• 117819-35-9 (R)-(-) ethyl 2-<3-(4-chlorobenzoyl)-4-methylphenoxy>propionate 

Relevant academic research and scientific papers

Asymmetric Synthesis of Optically Active 3-Cyclohexene-1-carboxylic Acid Utilizing Lactic Ester as a Chiral Auxiliary in the Diastereoselective Diels–Alder Reaction

The optically active 3-cyclohexene-1-carboxylic acid was synthesized through a TiCl4-catalyzed diastereoselective Diels–Alder reaction utilizing lactic acid ester as a chiral auxiliary, which can be removed by washing with H2O. The (S)- and (R)-isomers were both derived from easily available ethyl l-lactate.

Synthesis method of chiral fenoxanil

The invention relates to a synthesis method of chiral fenoxanil. The synthesis method of the chiral fenoxanil is characterized in that chiral ethyl lactate is subjected to sulfonylation reaction to obtain sulfonic acid ester; the sulfonic acid ester reacts with 2,4-dichlorophenol to generate 2-(2,4-dichlorophenoxy) ethyl propionate; the 2-(2,4-dichlorophenoxy) ethyl propionate and 2,-amino-2,3-dimethyl nitrile are subjected to ammonia ester exchange reaction to generate corresponding chiral fenoxanil, wherein the molar ratio of the 2-(2,4-dichlorophenoxy) ethyl propionate to the 2,-amino-2,3-dimethyl nitrile is 1:1 and the reaction temperature is 60 to 85 DEG C. The method is simple in synthesis route, hydrolysis and chlorination are not needed, little waste water and waste gas are generated, a high environmentally-friendly benefit is achieved, the production cost is greatly reduced, the condition is mild, the fenoxanil with optical chirality can be synthesized in an oriented mode by selecting different configuration of ethyl lactate, and important significance of further exploring the optical property of the fenoxanil is achieved.

PROCESS FOR PREPARING 2-FLUOROPROPIONALDEHYDE

A process comprising (i) providing a 2-fluoropropionic acid halide; (ii) hydrogenating the 2-fluoropropionic acid halide by contacting it with a heterogeneous hydrogenation catalyst in an atmosphere comprising hydrogen, obtaining a mixture comprising 2-fluoropropionic aldehyde.

Asymmetric synthesis and anti-protozoal activity of the 8,4′-oxyneolignans virolin, surinamensin and analogues

The asymmetric synthesis of 8,4′-oxyneolignans (-)-virolin, (-)-surinamensin and a number of analogues has been achieved. A divergent synthesis was used, with all compounds being elaborated from a single chiral aldehyde derived from ethyl lactate. In the

Synthesis of optically active α-(nonafluoro-tert-butoxy)carboxylic acids

Three novel α-(nonafluoro-tert-butoxy)carboxylic esters were synthesized by two methods: the Mitsunobu reaction of optically active (S)-α-hydroxycarboxylic esters and the Williamson synthesis starting from the corresponding O-mesyl derivatives. Both procedures from ethyl (S)-lactate resulted in the formation of a fluorous optically active (R)-lactic acid ester derivative, while the reactions from methyl (S)-mandelate took place with racemization. The proposed mechanism of this racemization is described. The conversion of methyl (S)-phenyllactate under Mitsunobu conditions was also stereospecific, but the reaction of its O-mesyl derivative yielded a mixture of substitution and elimination products. The optical purity of the α-(nonafluoro-tert-butoxy)carboxylic acids prepared by the hydrolysis of the above esters was determined by 1H NMR spectroscopy.

2,4-DIAMINO-6,7-DIHYDRO-5H-PYRROLO[2,3]PYRIMIDINE DERIVATIVES AS FAK/Pyk2 INHIBITORS

The invention relates to a novel class of 2,4-diamino-6,7-dihydro-5H-pyrrolo[2,3]pyrimidine derivatives as a FAK and/or Pyk2 inhibitor, to a process for their preparation, and to a composition thereof, as well as to use of the compounds for the inhibiting FAK and/or Pyk2 and method for the treatment of a FAK and/ or Pyk2 mediated disorder or disease.

Iron(III)-catalyzed halogenations by substitution of sulfonate esters

A novel halogenation reaction from sulfonates catalyzed by iron(III) is described. The reaction can be performed as a stoichiometric or a catalytic version. This reaction provides a convenient strategy for the efficient access to structurally diverse secondary chlorides, bromides and iodides. The stereochemical course of the reaction is governed by the substrate and the experimental conditions. Secondary alcohols modified as quisylates or pysylates are substantially more reactive. Aliphatic quisylates proceed with overall inversion of configuration under catalytic conditions. Chemoselectivity in bismesylates was observed in favour of the secondary mesylate. Additionally, based on the experimental results, a possible catalytic cycle for the halogenation has been proposed.

Synthesis of isatins with a chiral substituent at the nitrogen atom

(R)-Ethyl 2-(isatin-1-yl)propanoates 8a-c were prepared from the corresponding (R)-arylalanines by Sandmeyer's method in high yield and good enantioselectivity (up to 99%). The key step of the process is the Mitsunobu reaction.

Titanium mediated asymmetric aldol reaction with α-fluoropropionimide enolates

Aldol reaction utilising Evans N-(α-fluoropropyl)-2-oxazolidinones with TiCl4 have been explored. Reactions of N-(α-fluoropropyl)-2-oxazolidinones with aliphatic aldehydes generated α-fluoro-β-hydroxy-aldol products with high diastereoselectivi