2980-48-5

Usage

Uses

Used in Chemical Synthesis:
Methyl Epoxycrotonate is used as a key intermediate in the synthesis of various organic compounds, particularly in the pharmaceutical and agrochemical industries. Its unique epoxy and ester functional groups make it a valuable building block for the development of new molecules with potential biological activities.
Used in Biocatalysis:
Methyl Epoxycrotonate is utilized as a substrate in biocatalytic processes, where it can be transformed into other valuable compounds by the action of enzymes or whole cells. This application takes advantage of the selectivity and mild reaction conditions provided by biocatalysis, leading to more sustainable and environmentally friendly synthetic routes.
Used in Flavor and Fragrance Industry:
Methyl Epoxycrotonate is used as a starting material for the production of various flavor and fragrance compounds. Its ability to undergo a range of chemical reactions, such as epoxide opening and ester hydrolysis, allows for the creation of diverse scent profiles and flavor notes.
Used in Polymer Industry:
Methyl Epoxycrotonate is employed as a monomer in the synthesis of specialty polymers with unique properties, such as improved adhesion, enhanced mechanical strength, or tailored thermal stability. These polymers can be used in various applications, including coatings, adhesives, and composite materials.
Used in Environmental Applications:
Methyl Epoxycrotonate can be used in the development of biodegradable materials and products, such as plastics and packaging materials, due to its bio-based origin and susceptibility to enzymatic degradation. This application contributes to the reduction of plastic pollution and the promotion of a circular economy.

Upstream product

• 186581-53-3 diazomethane 
• 55058-23-6 (2R/3R)/(2S,3S)-2,3-epoxy-butanol 
• 75-91-2 tert.-butylhydroperoxide 
• 623-43-8 crotonic acid methyl ester 
• 132377-62-9 methyl 2-<(p-nitrobenzenesulfonyl)oxy>-3-hydroxybutanoate 
• 2443-40-5 trans-2,3-epoxybutanoic acid 
• 2443-40-5 trans-3-methyloxiranecarboxylic acid 
• 623-43-8 methyl crotonate 
• 132486-48-7 methyl 2-<(p-nitrobenzenesulfonyl)oxy>-3-hydroxybutanoate 
• 96613-68-2 (2S*,3R*)-methyl 2,3-dihydroxybutanoate 
• 67-56-1 methanol 
• 82769-14-0 ethyl trans-3-methyl-1-oxirane-2-carboxylate 
• 124716-78-5 Methyl 2-<<(p-nitrophenyl)sulfonyl>oxy>acetoacetate 

Downstream Products

• 117343-55-2 (+/-)-erythro-2,3-bis-(toluene-4-sulfonyloxy)-butyric acid methyl ester 
• 107686-09-9 methyl 3-methoxy-2-hydroxy butanoate 
• 107686-06-6 methyl 3-ethoxy-2-hydroxy butanoate 
• 107686-07-7 ethyl 3-ethoxy-2-hydroxy butanoate 
• 19780-35-9 ethyl 2,3-epoxybutanoate 
• 100945-79-7 trans-2,3-epoxy-1-(2,4,5-trimethoxyphenyl)-1-butanone 
• 73172-59-5 [(2RS,3SR)-3-methyloxiran-2-yl]phenylmethanone 
• 100992-78-7 trans-2,3-epoxy-1,1-diphenyl-1-butanol 
• 100939-25-1 α-(1-Hydroxyethyl)benzenessigsaeure-methylester 
• 129006-21-9 methyl 2-hydroxy-3-(p-methoxyphenoxy)butyrate 
• 36183-27-4 cis-2,2,5-Trimethyl-1,3-dioxolan-4-carbonsaeure-methylester 
• 82614-90-2 methyl 3-chloro-2-hydroxybutyrate 
• 129006-19-5 methyl 3-benzyloxy-2-hydroxybutyrate 
• 1487-49-6 3-hydroxybutyric acid methyl ester 

Relevant academic research and scientific papers

Kinetic Resolution of Racemic Aldehydes through Asymmetric Allenoate γ-Addition: Synthesis of (+)-Xylogiblactone A

A synthesis of (+)-xylogiblactone A has been achieved from t-butyl 2-methylbuta-2,3-dienoate in a linear three-step sequence. The key elements of the synthesis include a kinetic resolution of racemic 2-silyoxyaldehyde through the allenoate γ-addition to y

CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

METHOD FOR SYNTHESIZING SAPROPTERIN DIHYDROCHLORIDE

Disclosed is a method for synthesizing sapropterin dihydrochloride. The present disclosure reduces a synthesis route of the sapropterin dihydrochloride, and resolves a racemate intermediate or an intermediate having a low antimer isomerism value by using a chiral resolving reagent, thereby obtaining an intermediate having a high antimer isomerism value. Raw materials are cheap and readily available, and the cost is significantly reduced, hence providing an effective scheme for mass industrial production of the sapropterin dihydrochloride.

METHOD FOR SYNTHESIZING SAPROPTERIN DIHYDROCHLORIDE

Disclosed is a method for synthesizing sapropterin dihydrochloride. The present invention reduces a synthesis route of the sapropterin dihydrochloride, and resolves a racemate intermediate or an intermediate having a low antimer isomerism value by using a chiral resolving reagent, thereby obtaining an intermediate having a high antimer isomerism value. Raw materials are cheap and readily available, and the cost is significantly reduced, hence providing an effective scheme for mass industrial production of the sapropterin dihydrochloride.

New total synthesis of (±)-, (-)- and (+)-chuangxinmycins

(±)-2-Hydroxy-3-(1H-4′-iodoindol-3′-yl)butanoate 6 was stereoselectively converted into the (±)-(2,3)-syn-2-thioacetoxy ester 13 with retention of C2-stereochemistry in (±)-6. Palladium-catalyzed cyclization of indolyl iodide and the internal C2 thiol group of the substrate (±)-14 gave the (±)-cis methyl ester 2 of natural chuangxinmycin (1). Stereoselective total syntheses of (-)-(4S,5R)- and (+)-(4R,5S)-chuangxinmycins 1 were achieved based on the enzymatic syntheses of (2R,3S)- and (2S,3R)-epoxy butanoates 9, respectively. Chiral intermediates such as (2R,3S)- and (2S,3R)-2-hydroxy-3-(1H-4′-iodoindol-3′-yl)butanoate 6 for the chiral synthesis of (-)- and (+)-1 were also obtained by the enantioselective hydrolysis of the corresponding acetate (±)-16 by lipase.

New total synthesis of (±)-chuangxinmycin

(±)-4'-Iodoindolmycenate 6 was stereoselectively converted into the (±)-(2,3)-syn-2-thioacetoxy ester 16 with retention of C2-stereochemistry in (±)-6. Palladium-catalysed cyclisation of indolyl iodide and the internal C2 thiol group of the substrate (±)-17 derived from (±)-16 gave the (±)-cis methyl ester 2 of natural chuangxinmycin (1).

Synthesis and Reactions of 3-Hydroxy-2-nosyloxy Esters Produced by the Stereoselective Reduction of 2-Nosyloxy-3-keto Esters

The reduction of 2-nosyloxy-3-keto esters is an effective method for the preparation of 3-hydroxy-2-nosyloxy esters.The reduction is stereoselective for the syn isomer.The anti isomer can be produced as the major product by the addition of p-nitrobenzenesulfonyl peroxide to ketene bis-silyl acetal derivatives of 3-hydroxy esters.The diastereomers are separable chromatographically and can be converted stereospecifically to glycidic esters and 2-azido-3-hydroxy esters.As such they appear to have excellent potential as versatile synthetic intermediates for the synthesis of 1,2,3-trifunctional substances.

A stereocontrolled approach to electrophilic epoxides

Lithium t-butyl hydroperoxide (easily generated by addition of an alkyl-lithium to anhydrous t-butyl hydroperoxide in THF solution) is a powerful reagent for the epoxidation of electrophilic alkenes at -20 to 0 °C under full stereocontrol. Thus αβ-unsaturated esters, sulphones, sulphoximines, and amides are readily epoxidised with complete regio- and stereo-specificity and with considerable chiroselectivity (20-100%) when appropriate chiral auxiliaries such as menthyl, 8-phenylmenthyl, or a camphor-sulphonamide derivative are used. Asymmetric αβ-unsaturated sulphoximines undergo epoxidation with 100% diastereoselectivity. The only exceptions to stereocontrol noted are heavily substituted maleate esters such as di-t-butyl maleate. The αβ-epoxy amides are shown to be valuable sources of the corresponding epoxy ketones by treatment with an organolithium, allowing a stereo- and chemoselective entry in high yield to these useful intermediates.