5187-82-6

Usage

Uses

Used in Organic Chemistry:
(Ethoxycarbonylmethyl)dimethylsulfonium bromide is used as a reagent for the synthesis of α-sulfanyl-β-amino acid derivatives. It plays a crucial role in the formation of these compounds, which are important building blocks in the development of pharmaceuticals and other bioactive molecules.
Used in Nanocrystalline Magnesium Oxide Synthesis:
In the synthesis of α-sulfanyl-β-amino acid derivatives, (Ethoxycarbonylmethyl)dimethylsulfonium bromide is used in conjunction with nanocrystalline magnesium oxide. This combination enhances the efficiency and selectivity of the reaction, leading to the desired products with improved yields.
Used in Cyclopropanation Reactions:
(Ethoxycarbonylmethyl)dimethylsulfonium bromide is also utilized in the cyclopropanation of (-)-(S)-2-(p-tolylsulfinyl)cyclopent-2-enone. This reaction is an essential step in the synthesis of complex organic molecules, particularly those with cyclopropane rings, which are found in various natural products and pharmaceuticals.

InChI:InChI=1/C6H13O2S.BrH/c1-4-8-6(7)5-9(2)3;/h4-5H2,1-3H3;1H/q+1;/p-1

Upstream product

• 75-18-3 dimethylsulfide 
• 105-36-2 ethyl bromoacetate 
• 105-39-5 chloroacetic acid ethyl ester 
• 623-48-3 ethyl iodoacetae 

Downstream Products

• 123-29-5 ethyl pelargonate 
• 106-32-1 octanoic acid ethyl ester 
• 110-38-3 decanoic acid ethyl ester 
• 3556-76-1 ethyl (2Z)-3-phenyl-3-(phenylamino)prop-2-enoate 
• 4455-13-4 methylthioacetic acid ethyl ester 
• 4727-41-7 dimethylsulfonioacetate 
• 18322-54-8 ethyl cyclopentylacetate 
• 116872-31-2 1-methylthio-3-(α-furyl)-1,2-cyclopropanedicarboxylic acid diethyl ester 
• 124-40-3 dimethyl amine 
• 116947-40-1 1-methylthio-3-(3-pyridyl)-1,2-cyclopropanedicarboxylic acid diethyl ester 
• 116872-30-1 1-methylthio-3-(4-pyridyl)-1,2-cyclopropanedicarboxylic acid diethyl ester 
• 54340-71-5 (E)-ethyl hept-3-enoate 
• 624-78-2 N-Ethylmethylamine 
• 94117-87-0 1-methylthio-3-phenyl-1,2-cyclopropanedicarboxylic acid diethyl ester 

Relevant academic research and scientific papers

A Scaffold-Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides

A “branching–folding” synthetic strategy that affords a range of diverse cyclic benzo-sulfonamide scaffolds is presented. Whereas different annulation reactions on common ketimine substrates build the branching phase of the scaffold synthesis, a common hydrogenative ring-expansion method, facilitated by an increase of the ring-strain during the branching phase, led to sulfonamides bearing medium-sized rings in a folding pathway. Cell painting assay was successfully employed to identify tubulin targeting sulfonamides as novel mitotic inhibitors.

Metal-Free Multicomponent Reaction for Synthesis of 4,5-Disubstituted 1,2,3-(NH)-Triazoles

A metal-free domino reaction was developed for efficient synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles by sequentially coupling sulfur salts with aldehydes and sodium azide. In the presence of L-proline, olefinic sulfur salt intermediates rather than epoxides are formed in situ via the coupling of sulfur salts with aldehydes and cyclize with azide ion. This process features mild conditions, high efficiency, commercially available starting materials, and wide substrate scope. (Figure presented.).

Stereoselective Cyclopropanation of (-)-Levoglucosenone Derivatives Using Sulfonium and Sulfoxonium Ylides

The synthesis of tri- and tetrasubstituted cyclopropanes from 3-aryl-substituted levoglucosenones (LGO) has been developed. In contrast to the unstabilised ylide dimethylsulfonium methylide which gives epoxides from LGO via 1,2-addition, we have found that the soft nucleophile dimethylsulfoxonium methylide affords cyclopropanes in moderate yields from LGO and in excellent yields and stereoselectivity with 3-aryl LGO derivatives. The use of 1,1,3,3-tetramethylguanidine as base in DMSO to generate the ylide provided the best yields and shortest reaction times. Ester stabilised sulfonium ylides could also be used to generate tetrasubstituted cyclopropane derivatives. One of the products was converted into a cyclopropyl lactone via Baeyer-Villiger oxidation to demonstrate the utility of applying cyclopropanation chemistry to LGO. Georg Thieme Verlag Stuttgart.New York.

Diversity-oriented synthesis of cyclopropyl peptides from Ugi-derived dehydroalanines

A three-step synthesis of cyclopropyl peptides is reported. The protocol involves a consecutive Ugi-4CR/elimination reaction to prepare dehydroalanines followed by a Corey-Chaykovsky cyclopropanation reaction. Peptide-like molecules that resemble some pharmacologically active compounds with a variety of substituents in the cyclopropane ring were prepared. When (2-ethoxy-2-oxoethyl) dimethyl sulfonium ylide was used the reaction exclusively gives the cis-diastereoisomer cyclopropanes in good yields from readily prepared starting materials. A collection of 26 highly substituted cyclopropyl peptides were obtained.

Oxoindole derivative containing ternary spiro and synthetic method of oxoindole derivative

The invention discloses an oxoindole derivative containing ternary spiro. Four different isatin derivatives are respectively reacted with sulfur ylide so as to synthesize a three-membered ring product, the structural formulas of the sulfur ylide structure, isatin derivatives and three-membered ring product are respectively as shown in the specification; the four isatin derivatives are respectively as follows: R1 is methyl, R2 is ethyoxyl; R1 is methoxy group, R2 is methoxy group; R1 is chlorine, and R2 is ethyoxyl; R1 is methoxy group, R2 is ethyoxyl. The oxoindole derivative has the advantages that the three-membered cyclization reaction carried out between the sulfur ylide and the isatin derivatives is involved in the invention, and has the advantages of short reaction time, high yield and high selectivity.

Synthesis of fullerene C60monoadducts. Cyclopropanation of C60with sulfonium ylides

3′H-Cyclopropa[1,9](C60-Ih)[5,6]fullerene-3′-carboxylic acid can be synthesized in a good yield by cyclopropanation of fullerene C60with 2-(dimethyl-λ4-sulfanylidene)acetates provided that the ester residue is readily hydrolyzable in acid medium.

Development of multikilogram continuous flow cyclopropanation of N -benzylmaleimide through kinetic analysis

A convenient and high-yielding method for the synthesis of trans-(dioxo)-azabicyclo-[3.1.0]-hexane carboxylate, a key intermediate of complex molecules, is presented using a flow cyclopropanation process. From a detailed kinetic study, it is demonstrated that the reaction concentration, addition time of reagents, and initial mixing temperature are the critical parameters to minimize formation of byproducts and to get high reaction yield. Using a modular tubular flow reactor, the trans/cis-(dioxo)-azabicyclo-[3.1.0]-hexane carboxylate was obtained in 92% yield and isomerized under basic conditions to produce the trans-isomer in greater than 99% diastereomeric excess. Using this approach, the reaction yield was significantly increased compared to the batch process, and the robustness and reproducibility of this flow process was demonstrated for the synthesis of this key intermediate on a multikilogram scale.

PROCESS FOR THE SYNTHESIS OF SUBSTITUTED PYRAZOLES

A process for the preparation of 4,5-di- and 2,4,5-trisubstituted pyrazole 3-carboxylates from 3-acyloxirane-2-carboxylates and hydrazine compounds.

Synthesis of α-sulfanyl-β-amino acid derivatives by using nanocrystalline magnesium oxide

The Mannich-type reaction between alkyl, aryl and heterocyclic aldimines and sulfonium salts for the synthesis of α-sulfanyl-β-amino acid derivatives by using nanocrystalline magnesium oxide (NAP-MgO) is described. These products are obtained in moderate to high yields with moderate diastereoselectivities. The configuration of ethyl-3-{[(4-methylphenyl)sulfonyl] amino}-2-(methylsulfanyl)-3-(4-nitrophenyl)propanoate (major isomer) has been confirmed by X-ray diffraction technique to be anti, and consistent with the assignment based on 1H NMR spectroscopy. These α-sulfanyl- β-amino acid derivatives are important building blocks for pharmaceuticals with potent biological activity.

Preparation of chiral cyclopropanes with a carbohydrate fragment from levoglucosenone

Levoglucosenone (a chiral α,β-unsaturated ketone derivative of cellulose) underwent stereoselective cyclopropanation with sulfonium ylides to form chiral trisubstituted cyclopropanes annulated with the carbohydrate moiety in high yields.