Synthesis of Benzoboroxole for the Molecular Recognition of Carbohydrates

Synthesis of boronolectins as a sensor for the recognition of carbohydrates in vivo has significant applications in biochemical and biomedical science. Modern techniques for recognition of carbohydrates in vivo no longer rely on non-covalent interactions like hydrogen-bonding due to the competition of the sensor with both target and the excess water in the living system. The first step of the synthesis, the reaction between glycine methyl ester and methyl amine for the formation of glycine methyl amide, was achieved with an 89% yield. The second step of the synthesis was the reaction between the glycine methyl amide and pivalaldehyde in the presence of a catalyst (ytterbium triflate or H+) for the formation of a lactam. This reaction proved to be inconsistent