62269-44-7

Usage

Uses

Used in Organic Synthesis:
3-(TRIMETHYLSILYLOXY)CROTONIC ACID METHYL ESTER is used as a reagent for the preparation of other organic compounds, leveraging its reactivity to engage in multiple types of chemical reactions. Its role in organic synthesis is crucial for creating a broad spectrum of chemical entities.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 3-(TRIMETHYLSILYLOXY)CROTONIC ACID METHYL ESTER is utilized as a key building block. Its ability to undergo selective transformations makes it instrumental in the synthesis of complex organic molecules, contributing to the development of new drugs and medicinal compounds.
Used in Fine Chemicals Production:
3-(TRIMETHYLSILYLOXY)CROTONIC ACID METHYL ESTER is also employed in the production of fine chemicals, where its protective trimethylsilyloxy group allows for the synthesis of high-purity specialty chemicals that are vital in various applications, including fragrances, dyes, and other high-value products.
Overall, 3-(TRIMETHYLSILYLOXY)CROTONIC ACID METHYL ESTER's applications are diverse, reflecting its importance across different sectors of the chemical industry, from basic organic synthesis to the creation of sophisticated pharmaceuticals and fine chemicals.

InChI:InChI=1/C8H16O3Si/c1-7(6-8(9)10-2)11-12(3,4)5/h6H,1-5H3/b7-6+

Upstream product

• 26879-26-5 methyl 3-(O-trimethylsilyl)buten-2-oate 
• 105-45-3 acetoacetic acid methyl ester 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 67-56-1 methanol 
• 123347-59-1 2,2,6-Trimethyl-5-trimethylsilanyl-[1,3]dioxin-4-one 
• 75-77-4 chloro-trimethyl-silane 
• 43112-38-5 3-(trimethylsilyl)-2-oxazolidinone 
• 24589-78-4 N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 
• 33894-69-8 Methylester der γ-Iodmercuriacetessigsaeure 

Downstream Products

• 74590-73-1 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 
• 14629-58-4 trimethyl(phenethyloxy)silane 
• 124654-42-8 cis-methyl α-acetyltetrahydro-6-phenyl-2H-pyran-2-acetate 
• 119768-76-2 ethyl 2-benzoylamino-3-methoxycarbonyl-4-oxopentaonate 
• 880461-84-7 2-(1-methoxycarbonyl-2-oxo-propyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 174874-85-2 (2R,3S)-2-(3-acetoxy-1-benzyl-5-oxo-pyrrolidin-2-yl)-3-oxo-butyric acid methyl ester 
• 174874-87-4 (2R,3S)-2-<3-acetoxy-1-(4-methoxy-benzyl)-5-oxo-pyrrolidin-2-yl>-3-oxo-butyric acid methyl ester 
• 174874-86-3 (2R,3S)-2-<3-acetoxy-1-(3,4-dimethoxy-benzyl)-5-oxo-pyrrolidin-2-yl>-3-oxo-butyric acid methyl ester 
• 420-56-4 trimethylsilyl fluoride 
• 416857-11-9 2-(Methoxy-phenyl-methyl)-3-oxo-butyric acid methyl ester 
• 935248-46-7 9-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-7-(4-methoxy-benzyloxy)-8,8-dimethyl-3-oxo-nonanoic acid methyl ester 
• 935248-47-8 9-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-7-(4-methoxy-benzyloxy)-8,8-dimethyl-nonanoic acid methyl ester 
• 163852-89-9 methyl 1-(6-ethoxy-5,6-dihydro-2-methyl-1,4-oxathiin-3-yl)formate 

Relevant academic research and scientific papers

A Mass Spectrometric Study of the Dimethyl Ester Trimethylsilyl Enol Ether Derivatives of Some 3-Oxodicarboxylic Acids

The fragmentation pathways for the dimethyl ester trimethylsilyl enol ether derivatives of some 3-oxodicarboxylic acids have been found by using B/E and B2/E linked scans, collisional activated decomposition and isotope substitution techniques.The trimethylsilyloxy group strongly directs the decomposition processes, and induces a fragmentation pattern that intimately reflects the structure of the compounds.

Synthesis of (-)-Flavoskyrins by Catalyst-Free Oxidation of (R)-Configured Dihydroanthracenones in Aqueous Media and Its (Bio)synthetic Implications

A catalyst-free method for the synthesis of dimeric (-)-flavoskyrins has been developed. It involves the autoxidation of chemoenzymatically synthesized (R)-configured dihydroanthracenones in the presence of molecular oxygen in buffer of pH 6.0 followed by spontaneous [4 + 2] cycloaddition in stereocontrolled exo-anti fashion to form (-)-flavoskyrins. The method is applied to obtain several homo- A s well as heterodimerized flavoskyrins (nine examples) in 27-72% yield and implies the involvement of a similar pathway in the (bio)synthesis of modified bisanthraquinones and their analogues.

Monomeric Dihydroanthraquinones: A Chemoenzymatic Approach and its (Bio)synthetic Implications for Bisanthraquinones

Modified bisanthraquinones are complex dimeric natural products containing a cage-like structural motif. For their biosynthesis, monomeric dihydroanthraquinones have been proposed as key intermediates despite not being isolated from natural sources or synthesized as of yet. Here, isolation and characterization of dihydroemodin, as well as dihydrolunatin, synthesized by a biomimetic and chemoenzymatic approach using NADPH-dependent polyhydroxyanthracence reductase (PHAR) from Cochliobolus lunatus followed by Pb(OAc)4 oxidation is reported. Subsequent dimerization through a hetero-Diels–Alder reaction of the dihydroemodin and dihydrolunatin resulted in (?)-flavoskyrin (68 %) and (?)-lunaskyrin (62 %), respectively. Pyridine treatment of (?)-flavoskyrin and (?)-lunaskyrin gave (?)-rugulosin and (?)-2,2′-epi-cytoskyrin A in 64 % and 60 % yield, respectively, through a cascade that involves two dimeric intermediates. Implications of the described synthesis for the biosynthesis of bisanthraquinones by a combination of enzymatic and spontaneous steps are discussed.

New method for asymmetrically synthesizing natural product (-)-Euscapholide isomer

The invention relates to a new method for asymmetrically synthesizing a natural product (-)-Euscapholide isomer. The method comprises the following steps: carrying out methoxybenzyl group protection on (R)-3-hydroxymethyl butyrate used as an initial raw material, reducing by using diisobutylaluminium hydride, carrying out a Mukaiyama aldol reaction, reducing by using sodium borohydride, carrying out ring closure under acidic conditions, eliminating hydroxyl groups, and deprotecting to complete asymmetric total synthesis of the target molecule 1. The method has the advantages of novel and reasonable synthesis route design, cheap and easily available raw material, simple operating process, mild reaction conditions, efficient completion of the asymmetric total synthesis of the Euscapholide isomer with two chiral centers, and single product configuration.

Regio- and stereoselective nickel-catalyzed homoallylation of aldehydes with 1,3-dienes

Ni(acac)2 catalyzes homoallylation of aldehydes with 1,3-dienes in the presence of triethylborane. Triethylborane serves as a reducing agent delivering a formal hydride to the C2 position of 1,3-dienes, thus generating a formal homoallyl anion species and enabling the novel homoallylation of aldehydes. The reaction proceeds smoothly at room temperature in the absence of any phosphane or nitrogen ligands and is highly regioselective and stereoselective for a wide variety combination of aldehydes and 1,3-dienes: e.g., isoprene and benzaldehyde combine to give a mixture of anti- and syn-1-phenyl-3-methyl-4-penten-1-ol (2.2) in a ratio of 15:1 in 90% yield. Under the conditions, sterically congested aliphatic aldehydes and ketones show low yields. In such cases, diethylzinc serves as a substitute for triethylborane and yields the expected products in good yields with similarly high regio- and stereoselectivity. 1,3-Cyclohexadiene is one exception among 24 kinds of dienes examined and undergoes allylation (not homoallylation) selectively.

Neighboring group participation in Lewis acid-promoted [3 + 4] and [3 + 5] annulations. The synthesis of oxabicyclo[3.n.1]alkan-3-ones

Lewis acids are employed as catalysts in the annulation of 1,4- and 1,5-dicarbonyl dielectrophiles with bis(trimethylsilyl) end ethers of β-diketones and β-keto esters. A variety of 2-(alkoxycarbonyl)-m-oxabicyclo[3.n.1]alkan-3-ones can be constructed by this process in which two new carbon-carbon bonds are generated. Unusually high regiocontrol is observed, and good to excellent stereochemical control can be achieved at virtually every position on the new carbocycles. Intramolecular neighboring group participation is proposed to explain the unusually high selectivities attained in the annulation reaction.

Meerwein Saponification of Alkyl 3-Oxoalkanoates in the Gas Chromatograph

Alkyl 3-oxoalkanoates decompose by unevitable traces of water in the gas chromatograph to yield the corresponding methyl ketones and alcohols (Meerwein saponification).Decomposition occurs in the hot injector (T= 270 deg C) of the gas chromatograph and also on glass capillary columns (T> 160 deg C).Decomposition in routine work can be avoided by preparing the corresponding 3-trimethylsilyl enol ethers.