63696-99-1

Basic information

• Product Name: L(-)-METHANESULFONYLETHYLLACTATE
• Synonyms: L(-)-METHANESULFONYLETHYLLACTATE;ETHYL L(-)-METHANESULFONYLLACTATE;l(-)-methanesulfonylethyllactatetech90%;ethyl l(-)-lactate mesylate;ETHYL (2S)-2-METHYLSULFONYLOXYPROPANOATE;L-(-)-Methanesulfonyl ethyl lactate, 90%, tech;L(-)-Methanesulfonyl ethyl lactate, tech.;L(-)-Methanesulfonyl ethyl lactate, tech., 90% 25GR
• CAS NO: 63696-99-1
• Molecular Formula: C₆H₁₂O₅S
• Molecular Weight: 196.22
• Mol File: 63696-99-1.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 103-105 °C (0.2 mmHg)
• Flash Point: 137.6°C
• Appearance: /
• Density: 1.31
• Refractive Index: 1.5060 (estimate)
• CAS DataBase Reference: L(-)-METHANESULFONYLETHYLLACTATE(CAS DataBase Reference)
• NIST Chemistry Reference: L(-)-METHANESULFONYLETHYLLACTATE(63696-99-1)
• EPA Substance Registry System: L(-)-METHANESULFONYLETHYLLACTATE(63696-99-1)

Safety Data

• Hazard Codes: C
• Statements: 34-14
• Safety Statements: 8-45-36/37/39-25
• Hazardous Substances Data: 63696-99-1(Hazardous Substances Data)

Usage

Uses

Ethyl (S)-(-)-O-Mesyl Lactate is used as a reactant in the asymmetric synthesis of 8,4''-oxyneolignans virolin, surinamensin, and analogs with anti-protozoal activity.

Upstream product

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

Downstream Products

• 72959-94-5 (R)-(+)-ethyl 2-fluoropropionate 
• 117819-33-7 (R)-(+) ethyl 2-(3-benzoylphenoxy)propionate 
• 42253-99-6 ethyl (S)-2-phenylpropionate 
• 94202-83-2 ethyl (R)-2-(phenylselenyl)propionate 
• 454685-94-0 (S)-1-Allyl 4-ethyl 2-cyano-3-methylbutanedioate 
• 454685-94-0 (R)-1-Allyl 4-ethyl 2-cyano-3-methylbutanedioate 
• 272458-63-6 (S)-ethyl 2-(4-isobutylphenyl)propanoate 
• 84049-31-0 (2R,4S)-3-aza-2-methyl-4-phenyl-ethylpentanoate 
• 131775-56-9 (R)-2-(p-acetylphenoxy)propionic acid ethyl ester 
• 99967-64-3 (R)-2-(Benzylthio)propionsaeure-ethylester 
• 99967-66-5 (R)-2-(4-Chlorphenylthio)propionsaeure-ethylester 
• 66423-06-1 (R)-2-(2,4-Dichlorphenoxy)propionsaeure-ethylester 
• 1426163-17-8 (2R)-ethyl 2-(4'-bromo-2'-methoxyphenoxy)propanoate 
• 1312162-81-4 (S)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate 

Relevant articles and documents

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.

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.

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.