Modular solid-phase synthetic approach to optimize structural and electronic properties of oligo-boronic acid receptors and sensors for the aqueous recognition of oligosaccharides was written by Stones, Duane;Manku, Sukhdev;Lu, Xiaosong;Hall, Dennis G.. And the article was included in Chemistry – A European Journal in 2004.Synthetic Route of C12H16BBrO2 This article mentions the following:
This article describes the design and optimization of the first entirely modular, parallel solid-phase synthetic approach for the generation of well-defined polyamine oligo-boronic acid receptors and fluorescence sensors for complex oligosaccharides. The synthetic approach allows an effective building of the receptor polyamine backbone, followed by the controlled diversification of the amine benzylic side chains. This approach enabled the testing, in a modular fashion, of the effect of different aryl-boronic acid units substituted with un-encumbering para electron-withdrawing or electron-donating groups. The feasibility of this approach toward automated synthesis was also investigated with the assembly of a sub-library of receptors by means of the Irori MiniKan technol. Several sub-libraries of anthracene-capped sensors containing two or three aryl-boronic acids were synthesized, and their binding to a series of model disaccharides was examined in neutral aqueous media. The calculation of association constants by fluorescence titrations confirmed that subtle changes in the structures of the inter-amine spacers in the polyamine backbone can have a significant effect on the stability of the resulting complexes. Most importantly, this study led to the determination of the preferred electronic characteristics for the aryl-boronate units, and suggests that a new generation of receptors containing very electron-poor aryl-boronic acids could lead to a significant improvement of binding affinities. In the experiment, the researchers used many compounds, for example, 2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1Synthetic Route of C12H16BBrO2).
2-(2-(Bromomethyl)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane (cas: 166821-88-1) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Synthetic Route of C12H16BBrO2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary