Benzoxaborate Protecting Groups

This invention can be a useful synthetic tool for any company / laboratory that is pursuing the synthesis of benzoxaborole-containing targets. Reagents can be commercialized through a chemical supply company making them available for purchase by academic labs and / or companies.

This invention currently is in laboratory use.

Opportunity

The Tomsho Lab has synthesized zwitterionic benzoxaborole complexes that can be used in mild oxidation reactions, substitution conditions, and mild reductive conditions in good yields compared to the literature. Solubility in organic solvents also improved, which facilitated reactions where the unprotected substrate was not soluble.

Due to synthetic struggles while pursuing benzoxaborole-containing analogs of a natural product, Dr. Tomsho and his colleagues searched the literature to seek potential protecting groups of the benzoxaborole functionality. One 2013 report described benzoxaborole protection, however the stability of this group was very limited.

The team has reported the design, synthesis and evaluation of two families of compounds that form divalent, zwitterionic complexes with benzoxaboroles. These compounds efficiently and reversibly protect the benzoxaborole functionality through one or more chemical steps that are incompatible with the unprotected benzoxaborole. The chemical robustness of these protecting groups has been characterized and it was determined that these protecting groups offered improved reaction scope diversity when compared with the previous state of the art.

Unique Attributes

After initial investigation, the Tomsho team created a rigidified and semi-conjugated system that exhibits enhanced stability to reaction conditions and to common synthetic manipulations (i.e., extractions, flash chromatography).

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