1105069-27-9

Usage

Uses

Used in Small Molecule Synthesis:
(E)-2-bromovinylboronic acid N-methyliminodiacetic ester is used as a building block for the incorporation of cis-olefin structures in small molecule synthesis. Its unique reactivity allows for the creation of complex polyene-containing natural product motifs, which can be utilized in various applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (E)-2-bromovinylboronic acid N-methyliminodiacetic ester is used as a key intermediate in the development of new drugs and therapeutic agents. Its ability to form cis-olefin structures makes it a valuable component in the synthesis of bioactive compounds with potential medicinal properties.
Used in Chemical Research:
(E)-2-bromovinylboronic acid N-methyliminodiacetic ester is also used in chemical research as a tool to study the properties and reactions of cis-olefin-containing compounds. Its unique structure allows researchers to explore new reaction pathways and develop innovative synthetic methods for the preparation of complex molecules.

Upstream product

• 4408-64-4 N-methyliminodiacetic acid 
• 114701-85-8 (E)-(2-bromoethenyl)dibromoborane 
• 41309-43-7 (2-bromovinyl)trimethylsilane 
• 71160-37-7 sodium methyliminodiacetate 

Downstream Products

• 736987-78-3 trans-2-(2,4-difluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Vinyl MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis

Iterative cross-coupling represents a potentially general approach for the simple, efficient, and flexible construction of natural products, pharmaceuticals, and materials. N-Methyliminodiacetic acid (MIDA) boronates represent a promising platform for the

SYSTEM FOR CONTROLLING THE REACTIVITY OF BORONIC ACIDS

A protected organoboronic acid includes a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. A method of performing a chemical reaction includes contacting a protected organoboronic acid with a reagent, the protected organoboronic acid including a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. The organic group is chemically transformed, and the boron is not chemically transformed.

Simple, efficient, and modular syntheses of polyene natural products via iterative cross-coupling

This communication describes the discovery of air-stable and highly versatile B-protected haloalkenylboronic acid building blocks for iterative cross-coupling. These reagents enable the total synthesis of polyene natural products with extraordinary levels of simplicity, efficiency, and modularity. Specifically, all-trans-retinal, β-parinaric acid, and one-half of the amphotericin B macrolide skeleton were prepared using only the Suzuki-Miyaura reaction in an iterative manner to bring together collections of simple and readily accessible building blocks. In contrast to their boronic acid counterparts, the intermediate polyenylboronate esters are remarkably stable (to both column purification and storage), which is critical to their successful utilization. Moreover, the reactive boronic acids can be cleanly liberated using very mild aqueous base. These advances have enabled preparation of the longest polyene ever synthesized using the SM reaction. We additionally report, to the best of our knowledge, the first triply metal selective (Zn vs Sn and B) cross-coupling reaction, the first selective cross-coupling with a differentially ligated diboron reagent, and the first cross-couplings between polyenylchlorides and vinylboronic acids. Collectively, these new building blocks and methods can dramatically improve the way polyene natural products and their derivatives are synthesized in the laboratory. Copyright